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SUPPORTING INFORMATION
REGULAR ARTICLE
Metal Free Synthesis of Functionalized 1-Aryl Isoquinolines via
Iodine Mediated Oxidative Dehydrogenation and Ring Opening of
Lactam in Isoindoloisoquinolinones
KAMSALI MURALI MOHAN ACHARI, MUTHUPANDI KARTHICK, CHINNASAMY
RAMARAJ RAMANATHAN*
Department of Chemistry, Pondicherry University, Puducherry – 605 014, India.
E-mail: [email protected]
Table of contents1H and 13C NMR spectra of Compound (3a) in Table 2 S1
1H and 13C NMR spectra of Compound (3b) in Table 2 S2
1H and 13C NMR spectra of Compound (3c) in Table 2 S3
1H and 13C NMR spectra of Compound (3e) in Table 2 S4
1H and 13C NMR spectra of Compound (3f) in Table 2 S51H and 13C NMR spectra of Compound (3g) in Table 2 S61H and 13C NMR spectra of Compound (3h) in Table 2 S71H and 13C NMR spectra of Compound (3j) in Table 2 S81H and 13C NMR spectra of Compound (2a) in Table 3 S91H and 13C NMR spectra of Compound (2b) in Table 3 S101H and 13C NMR spectra of Compound (2c) in Table 3 S111H and 13C NMR spectra of Compound (2d) in Table 3 S121H and 13C NMR spectra of Compound (2e) in Table 3 S131H NMR spectra of Compound (2f) in Table 3 S141H NMR spectra of Compound (2g) in Table 3 S151H and 13C NMR spectra of Compound (2h) in Table 3 S161H and 13C NMR spectra of Compound (2i) in Table 3 S171H and 13C NMR spectra of Compound (4a) in Table 3 S181H and 13C NMR spectra of Compound (4c) in Table 3 S191H and 13C NMR spectra of Compound (4e) in Table 3 S201H and 13C NMR spectra of Compound (4h) in Table 3 S211H and 13C NMR spectra of Compound (A) S221H and 13C NMR spectra of Compound (B) S231H and 13C NMR spectra of Compound (C) S24
180 160 140 120 100 80 60 40 20 ppm
29.32
35.15
50.58
76.84
77.16
77.48
90.44
101.36
107.46
108.92
123.53
123.91
128.90
129.01
129.95
132.30
132.48
144.20
146.70
147.90
167.83
Current Data ParametersNAME MK-7A-IEXPNO 2PROCNO 1
F2 - Acquisition ParametersDate_ 20161213Time 15.23INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zgpg30TD 65536SOLVENT CDCl3NS 256DS 4SWH 24038.461 HzFIDRES 0.366798 HzAQ 1.3631988 secRG 32DW 20.800 usecDE 6.00 usecTE 294.5 KD1 2.00000000 secd11 0.03000000 secDELTA 1.89999998 secTD0 1
======== CHANNEL f1 ========NUC1 13CP1 9.15 usecPL1 0.00 dBSFO1 100.6228298 MHz
======== CHANNEL f2 ========CPDPRG2 waltz16NUC2 1HPCPD2 90.00 usecPL12 14.90 dBPL13 14.90 dBPL2 -3.00 dBSFO2 400.1316005 MHz
F2 - Processing parametersSI 32768SF 100.6127560 MHzWDW EMSSB 0LB 1.00 HzGB 0PC 1.40
C13CPD CDCl3 {D:\CRR} KOPAL 1
20406080100120140160180 ppm
29.05
35.30
50.59
55.96
76.84
77.16
77.48
90.12
109.45
115.51
125.01
125.20
126.87
127.35
128.68
129.47
135.10
135.91
146.39
163.47
167.91
Current Data ParametersNAME MK-83EXPNO 2PROCNO 1
F2 - Acquisition ParametersDate_ 20161220Time 12.45INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zgpg30TD 65536SOLVENT CDCl3NS 256DS 4SWH 24038.461 HzFIDRES 0.366798 HzAQ 1.3631988 secRG 32DW 20.800 usecDE 6.00 usecTE 293.9 KD1 2.00000000 secd11 0.03000000 secDELTA 1.89999998 secTD0 1
======== CHANNEL f1 ========NUC1 13CP1 9.15 usecPL1 0.00 dBSFO1 100.6228298 MHz
======== CHANNEL f2 ========CPDPRG2 waltz16NUC2 1HPCPD2 90.00 usecPL12 14.90 dBPL13 14.90 dBPL2 -3.00 dBSFO2 400.1316005 MHz
F2 - Processing parametersSI 32768SF 100.6127575 MHzWDW EMSSB 0LB 1.00 HzGB 0PC 1.40
C13CPD CDCl3 {D:\CRR} KOPAL 1
10 9 8 7 6 5 4 3 2 1 0 ppm
1.132
1.664
1.681
2.828
2.858
2.865
2.868
2.876
3.013
3.036
3.050
3.357
3.369
3.385
3.390
3.397
3.401
3.418
3.429
3.932
4.358
4.364
4.373
4.380
4.390
4.397
4.406
4.412
7.004
7.009
7.025
7.030
7.148
7.165
7.226
7.230
7.244
7.248
7.260
7.267
7.283
7.286
7.385
7.390
7.748
7.769
7.812
7.815
7.830
7.835
1.09
2.80
1.00
1.00
2.99
1.01
0.95
1.01
2.32
0.97
0.87
1.00
Current Data ParametersNAME MK-83EXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20161220Time 11.52INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zg30TD 65536SOLVENT CDCl3NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9846387 secRG 203DW 60.800 usecDE 6.00 usecTE 293.8 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 11.42 usecPL1 -3.00 dBSFO1 400.1324710 MHz
F2 - Processing parametersSI 32768SF 400.1300051 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00
PROTON CDCl3 {D:\CRR} KOPAL 1
180 160 140 120 100 80 60 40 20 ppm
21.17
29.11
35.16
50.54
76.84
77.16
77.48
90.42
123.69
123.80
127.42
127.72
129.86
129.97
132.38
132.41
133.01
134.75
138.63
144.27
167.84
Current Data ParametersNAME MK-40EXPNO 2PROCNO 1
F2 - Acquisition ParametersDate_ 20160909Time 15.26INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zgpg30TD 65536SOLVENT CDCl3NS 200DS 4SWH 24038.461 HzFIDRES 0.366798 HzAQ 1.3631988 secRG 45.2DW 20.800 usecDE 6.00 usecTE 294.7 KD1 2.00000000 secd11 0.03000000 secDELTA 1.89999998 secTD0 1
======== CHANNEL f1 ========NUC1 13CP1 9.15 usecPL1 0.00 dBSFO1 100.6228298 MHz
======== CHANNEL f2 ========CPDPRG2 waltz16NUC2 1HPCPD2 90.00 usecPL12 14.90 dBPL13 14.90 dBPL2 -3.00 dBSFO2 400.1316005 MHz
F2 - Processing parametersSI 32768SF 100.6127573 MHzWDW EMSSB 0LB 1.00 HzGB 0PC 1.40
C13CPD CDCl3 {D:\CRR} KOPAL 1
10 9 8 7 6 5 4 3 2 1 0 ppm
2.290
2.836
2.841
2.970
3.031
3.367
3.379
3.396
3.400
3.407
3.411
3.428
3.440
4.385
4.391
4.401
4.407
4.417
4.424
4.433
4.439
6.972
7.080
7.100
7.260
7.486
7.488
7.505
7.507
7.523
7.525
7.610
7.613
7.629
7.632
7.648
7.651
7.728
7.748
7.822
7.824
7.826
7.841
7.843
7.845
7.898
7.917
3.09
1.12
2.74
1.23
1.02
1.07
1.04
1.09
0.99
1.02
1.02
1.03
1.00
PROTON CDCl3 {D:\CRR} KOPAL 1Current Data ParametersNAME MK-40EXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20160909Time 15.14INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zg30TD 65536SOLVENT CDCl3NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9846387 secRG 114DW 60.800 usecDE 6.00 usecTE 294.1 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 11.42 usecPL1 -3.00 dBSFO1 400.1324710 MHz
F2 - Processing parametersSI 32768SF 400.1300051 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00
180 160 140 120 100 80 60 40 20 ppm
22.97
34.62
50.46
56.23
60.62
60.85
76.84
77.16
77.48
90.12
106.63
122.03
123.41
123.91
129.95
130.98
132.37
132.43
142.58
144.10
151.16
152.25
167.58
Current Data ParametersNAME MK-38-2,3,4-OMEEXPNO 2PROCNO 1
F2 - Acquisition ParametersDate_ 20160830Time 16.16INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zgpg30TD 65536SOLVENT CDCl3NS 91DS 4SWH 24038.461 HzFIDRES 0.366798 HzAQ 1.3631988 secRG 32DW 20.800 usecDE 6.00 usecTE 294.2 KD1 2.00000000 secd11 0.03000000 secDELTA 1.89999998 secTD0 1
======== CHANNEL f1 ========NUC1 13CP1 9.15 usecPL1 0.00 dBSFO1 100.6228298 MHz
======== CHANNEL f2 ========CPDPRG2 waltz16NUC2 1HPCPD2 90.00 usecPL12 14.90 dBPL13 14.90 dBPL2 -3.00 dBSFO2 400.1316005 MHz
F2 - Processing parametersSI 32768SF 100.6127623 MHzWDW EMSSB 0LB 1.00 HzGB 0PC 1.40
C13CPD CDCl3 {D:\CRR} KOPAL 1
10 9 8 7 6 5 4 3 2 1 0 ppm
2.773
2.788
2.801
2.817
2.872
2.877
2.883
2.888
2.918
2.925
3.255
3.267
3.285
3.288
3.297
3.300
3.317
3.329
3.789
3.814
3.916
4.420
4.425
4.436
4.441
4.453
4.458
4.468
4.473
7.180
7.260
7.491
7.492
7.510
7.511
7.528
7.530
7.614
7.617
7.633
7.636
7.652
7.655
7.828
7.846
7.861
7.880
1.04
1.09
2.91
1.00
3.04
2.91
3.07
1.01
0.96
1.00
1.02
2.00
PROTON CDCl3 {D:\CRR} KOPAL 1Current Data ParametersNAME MK-38-2,3,4-OMEEXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20160830Time 16.14INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zg30TD 65536SOLVENT CDCl3NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9846387 secRG 71.8DW 60.800 usecDE 6.00 usecTE 293.6 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 11.42 usecPL1 -3.00 dBSFO1 400.1324710 MHz
F2 - Processing parametersSI 32768SF 400.1300049 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00
200 180 160 140 120 100 80 60 40 20 ppm
24.09
33.83
50.32
55.99
56.19
76.84
77.16
77.48
91.93
110.40
110.72
123.23
125.65
126.79
126.85
129.81
131.88
132.89
144.07
151.61
152.45
167.60
Current Data ParametersNAME MK-65-IEXPNO 2PROCNO 1
F2 - Acquisition ParametersDate_ 20161024Time 11.07INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zgpg30TD 65536SOLVENT CDCl3NS 256DS 4SWH 24038.461 HzFIDRES 0.366798 HzAQ 1.3631988 secRG 28.5DW 20.800 usecDE 6.00 usecTE 293.5 KD1 2.00000000 secd11 0.03000000 secDELTA 1.89999998 secTD0 1
======== CHANNEL f1 ========NUC1 13CP1 9.15 usecPL1 0.00 dBSFO1 100.6228298 MHz
======== CHANNEL f2 ========CPDPRG2 waltz16NUC2 1HPCPD2 90.00 usecPL12 14.90 dBPL13 14.90 dBPL2 -3.00 dBSFO2 400.1316005 MHz
F2 - Processing parametersSI 32768SF 100.6127568 MHzWDW EMSSB 0LB 1.00 HzGB 0PC 1.40
C13CPD CDCl3 {D:\CRR} KOPAL 1
10 9 8 7 6 5 4 3 2 1 0 ppm
2.752
2.782
2.783
2.888
2.896
2.899
2.932
2.986
3.198
3.209
3.231
3.241
3.258
3.263
3.740
3.960
4.448
4.450
4.463
4.466
4.480
4.483
4.496
4.499
6.747
6.770
6.795
6.817
7.260
7.457
7.459
7.475
7.478
7.494
7.496
7.534
7.537
7.553
7.556
7.572
7.575
7.803
7.805
7.806
7.822
7.824
7.825
7.826
8.270
8.289
1.14
1.07
3.02
1.15
3.20
3.11
1.03
2.06
1.07
1.07
1.04
1.00
Current Data ParametersNAME MK-65-IIEXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20161026Time 14.07INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zg30TD 65536SOLVENT CDCl3NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9846387 secRG 228DW 60.800 usecDE 6.00 usecTE 293.2 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 11.42 usecPL1 -3.00 dBSFO1 400.1324710 MHz
F2 - Processing parametersSI 32768SF 400.1300051 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00
PROTON CDCl3 {D:\CRR} KOPAL 1
180 160 140 120 100 80 60 40 20 ppm
28.84
34.73
50.50
76.84
77.16
77.48
90.10
122.63
123.52
123.89
129.16
129.95
130.09
132.09
132.24
132.52
134.95
137.10
143.58
167.62
Current Data ParametersNAME MK-46EXPNO 2PROCNO 1
F2 - Acquisition ParametersDate_ 20160919Time 12.27INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zgpg30TD 65536SOLVENT CDCl3NS 150DS 4SWH 24038.461 HzFIDRES 0.366798 HzAQ 1.3631988 secRG 32DW 20.800 usecDE 6.00 usecTE 293.9 KD1 2.00000000 secd11 0.03000000 secDELTA 1.89999998 secTD0 1
======== CHANNEL f1 ========NUC1 13CP1 9.15 usecPL1 0.00 dBSFO1 100.6228298 MHz
======== CHANNEL f2 ========CPDPRG2 waltz16NUC2 1HPCPD2 90.00 usecPL12 14.90 dBPL13 14.90 dBPL2 -3.00 dBSFO2 400.1316005 MHz
F2 - Processing parametersSI 32768SF 100.6127653 MHzWDW EMSSB 0LB 1.00 HzGB 0PC 1.40
C13CPD CDCl3 {D:\CRR} KOPAL 1
10 9 8 7 6 5 4 3 2 1 0 ppm
2.836
2.840
2.957
3.016
3.337
3.348
3.365
3.369
3.376
3.381
3.397
4.372
4.379
4.388
4.394
4.405
4.411
4.420
4.427
7.260
7.295
7.297
7.300
7.363
7.368
7.384
7.389
7.494
7.497
7.513
7.515
7.532
7.534
7.612
7.615
7.631
7.634
7.650
7.653
7.691
7.712
7.829
7.831
7.847
7.849
7.866
7.868
0.97
2.80
1.20
1.00
0.98
0.94
0.94
0.97
0.97
0.96
1.93
PROTON CDCl3 {D:\CRR} KOPAL 1Current Data ParametersNAME MK-46EXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20160919Time 12.20INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zg30TD 65536SOLVENT CDCl3NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9846387 secRG 64DW 60.800 usecDE 6.00 usecTE 293.2 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 11.42 usecPL1 -3.00 dBSFO1 400.1324710 MHz
F2 - Processing parametersSI 32768SF 400.1300048 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.0010 9 8 7 6 5 4 3 2 1 0 ppm
2.70
52.71
12.71
62.72
22.74
62.75
22.75
72.76
32.93
02.95
82.97
22.98
52.99
93.01
43.32
23.33
33.35
03.35
43.36
23.36
53.38
33.39
44.36
84.37
44.38
34.38
94.40
14.40
74.41
64.42
25.89
45.89
75.92
85.93
16.58
27.26
07.30
57.49
67.51
57.53
37.61
77.61
97.63
67.63
87.65
57.65
77.83
17.84
07.85
07.85
9
1.09
3.33
0.63
0.99
1.05
2.04
0.97
0.97
1.00
1.00
1.99
Current Data ParametersNAME MK-79-IEXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20161212Time 12.34INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zg30TD 65536SOLVENT CDCl3NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9846387 secRG 203DW 60.800 usecDE 6.00 usecTE 293.4 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 11.42 usecPL1 -3.00 dBSFO1 400.1324710 MHz
F2 - Processing parametersSI 32768SF 400.1300051 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00
PROTON CDCl3 {D:\CRR} KOPAL 1
10 9 8 7 6 5 4 3 2 1 0 ppm
-0.001
1.256
2.860
2.867
2.890
2.900
2.908
2.989
3.031
3.047
3.059
3.074
3.394
3.405
3.422
3.426
3.433
3.438
3.454
3.466
4.399
4.405
4.414
4.421
4.431
4.438
4.447
4.453
7.152
7.169
7.231
7.245
7.249
7.260
7.267
7.282
7.301
7.502
7.520
7.539
7.626
7.643
7.662
7.839
7.857
7.915
7.934
1.08
2.96
1.12
1.01
1.01
0.95
2.39
0.99
0.99
1.91
1.00
PROTON CDCl3 {D:\CRR} KOPAL 1Current Data ParametersNAME MMA-II-407-1EXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20141127Time 12.41INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zg30TD 65536SOLVENT CDCl3NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9846387 secRG 181DW 60.800 usecDE 6.00 usecTE 297.6 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 11.42 usecPL1 -3.00 dBSFO1 400.1324710 MHz
F2 - Processing parametersSI 32768SF 400.1300052 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00
180 160 140 120 100 80 60 40 20 ppm
29.11
35.18
50.56
76.84
77.16
77.48
90.49
123.78
123.83
126.87
127.54
128.70
129.47
129.95
132.40
132.50
134.93
135.92
144.08
167.81
Current Data ParametersNAME MMA-II-407-1EXPNO 2PROCNO 1
F2 - Acquisition ParametersDate_ 20141128Time 9.59INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zgpg30TD 65536SOLVENT CDCl3NS 512DS 4SWH 24038.461 HzFIDRES 0.366798 HzAQ 1.3631988 secRG 32DW 20.800 usecDE 6.00 usecTE 296.5 KD1 2.00000000 secd11 0.03000000 secDELTA 1.89999998 secTD0 1
======== CHANNEL f1 ========NUC1 13CP1 9.15 usecPL1 0.00 dBSFO1 100.6228298 MHz
======== CHANNEL f2 ========CPDPRG2 waltz16NUC2 1HPCPD2 90.00 usecPL12 14.90 dBPL13 14.90 dBPL2 -3.00 dBSFO2 400.1316005 MHz
F2 - Processing parametersSI 32768SF 100.6127572 MHzWDW EMSSB 0LB 1.00 HzGB 0PC 1.40
C13CPD CDCl3 {D:\CRR} KOPAL 1
12 11 10 9 8 7 6 5 4 3 2 1 0 ppm
2.697
2.701
2.708
2.712
2.737
2.742
2.748
2.752
2.969
2.982
2.997
3.012
3.022
3.037
3.328
3.339
3.360
3.371
3.390
3.402
3.468
3.469
3.830
3.845
3.941
4.422
4.426
4.437
4.441
4.454
4.459
4.470
4.474
6.595
7.260
7.332
7.494
7.512
7.513
7.531
7.531
7.620
7.623
7.639
7.642
7.658
7.660
7.830
7.849
7.865
7.884
1.10
3.01
1.01
1.00
3.11
3.33
1.07
1.05
0.97
1.00
1.02
2.04
Current Data ParametersNAME MK-64-IIEXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20161020Time 11.20INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zg30TD 65536SOLVENT CDCl3NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9846387 secRG 128DW 60.800 usecDE 6.00 usecTE 293.1 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 11.42 usecPL1 -3.00 dBSFO1 400.1324710 MHz
F2 - Processing parametersSI 32768SF 400.1300051 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00
PROTON CDCl3 {D:\CRR} KOPAL 1
30405060708090100110120130140150160170180 ppm
28.89
35.12
50.54
56.01
56.23
76.84
77.16
77.48
90.26
110.35
111.55
123.31
123.94
127.62
127.65
129.88
132.35
132.44
144.42
147.99
149.41
167.80
Current Data ParametersNAME MK-64-IIEXPNO 2PROCNO 1
F2 - Acquisition ParametersDate_ 20161020Time 11.37INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zgpg30TD 65536SOLVENT CDCl3NS 256DS 4SWH 24038.461 HzFIDRES 0.366798 HzAQ 1.3631988 secRG 32DW 20.800 usecDE 6.00 usecTE 293.9 KD1 2.00000000 secd11 0.03000000 secDELTA 1.89999998 secTD0 1
======== CHANNEL f1 ========NUC1 13CP1 9.15 usecPL1 0.00 dBSFO1 100.6228298 MHz
======== CHANNEL f2 ========CPDPRG2 waltz16NUC2 1HPCPD2 90.00 usecPL12 14.90 dBPL13 14.90 dBPL2 -3.00 dBSFO2 400.1316005 MHz
F2 - Processing parametersSI 32768SF 100.6127579 MHzWDW EMSSB 0LB 1.00 HzGB 0PC 1.40
C13CPD CDCl3 {D:\CRR} KOPAL 1
Figure S1- 1H and 13C NMR spectra of compound (3a)
Figure S2- 1H and 13C NMR spectra of compound (3b)
180 160 140 120 100 80 60 40 20 ppm
38.89
39.10
39.31
39.52
39.73
39.94
40.15
55.20
55.72
105.09
105.83
117.98
123.03
127.38
128.11
129.18
130.14
132.08
138.94
140.38
140.73
149.08
152.00
160.56
171.89
Current Data ParametersNAME MMA-II-492EXPNO 4PROCNO 1
F2 - Acquisition ParametersDate_ 20150803Time 17.23INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zgpg30TD 65536SOLVENT DMSONS 1024DS 4SWH 24038.461 HzFIDRES 0.366798 HzAQ 1.3631988 secRG 114DW 20.800 usecDE 6.00 usecTE 297.5 KD1 2.00000000 secd11 0.03000000 secDELTA 1.89999998 secTD0 1
======== CHANNEL f1 ========NUC1 13CP1 9.15 usecPL1 0.00 dBSFO1 100.6228298 MHz
======== CHANNEL f2 ========CPDPRG2 waltz16NUC2 1HPCPD2 90.00 usecPL12 14.90 dBPL13 14.90 dBPL2 -3.00 dBSFO2 400.1316005 MHz
F2 - Processing parametersSI 32768SF 100.6128075 MHzWDW EMSSB 0LB 1.00 HzGB 0PC 1.40
C13CPD DMSO {D:\CRR} KOPAL 1
180 160 140 120 100 80 60 40 20 ppm
38.89
39.10
39.31
39.52
39.73
39.94
40.15
119.02
125.20
125.63
128.00
128.72
128.86
129.95
130.73
131.57
132.04
134.84
136.48
139.55
142.84
160.92
167.70
Current Data ParametersNAME MMA-II-442EXPNO 4PROCNO 1
F2 - Acquisition ParametersDate_ 20150803Time 12.35INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zgpg30TD 65536SOLVENT DMSONS 1024DS 4SWH 24038.461 HzFIDRES 0.366798 HzAQ 1.3631988 secRG 57DW 20.800 usecDE 6.00 usecTE 297.9 KD1 2.00000000 secd11 0.03000000 secDELTA 1.89999998 secTD0 1
======== CHANNEL f1 ========NUC1 13CP1 9.15 usecPL1 0.00 dBSFO1 100.6228298 MHz
======== CHANNEL f2 ========CPDPRG2 waltz16NUC2 1HPCPD2 90.00 usecPL12 14.90 dBPL13 14.90 dBPL2 -3.00 dBSFO2 400.1316005 MHz
F2 - Processing parametersSI 32768SF 100.6128126 MHzWDW EMSSB 0LB 1.00 HzGB 0PC 1.40
C13CPD DMSO {D:\CRR} KOPAL 1
11 10 9 8 7 6 5 4 3 2 1 ppm2.491
2.495
2.500
2.505
2.509
3.358
7.441
7.443
7.459
7.462
7.571
7.575
7.626
7.630
7.645
7.649
7.664
7.668
7.698
7.701
7.716
7.720
7.735
7.739
7.795
7.800
7.808
7.809
7.814
8.002
8.004
8.020
8.024
8.168
8.170
8.174
8.304
8.524
8.538
1.00
1.70
1.08
1.19
1.07
1.05
0.82
1.04
PROTON DMSO {D:\CRR} KOPAL 1Current Data ParametersNAME MMA-II-442EXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20150803Time 11.55INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zg30TD 65536SOLVENT DMSONS 64DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9846387 secRG 181DW 60.800 usecDE 6.00 usecTE 297.2 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 11.42 usecPL1 -3.00 dBSFO1 400.1324710 MHz
F2 - Processing parametersSI 32768SF 400.1299970 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00
11 10 9 8 7 6 5 4 3 2 1 ppm2.491
2.495
2.500
2.505
2.509
3.355
3.369
7.412
7.414
7.430
7.433
7.545
7.547
7.560
7.562
7.565
7.594
7.598
7.613
7.617
7.632
7.636
7.661
7.665
7.680
7.684
7.699
7.702
7.721
7.726
7.736
7.741
7.747
7.756
7.762
7.789
7.803
7.977
7.995
8.015
8.471
1.05
2.26
1.25
1.29
1.22
1.07
2.09
1.00
PROTON DMSO {D:\CRR} KOPAL 1Current Data ParametersNAME MMA-II-399-3EXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20141115Time 19.37INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zg30TD 65536SOLVENT DMSONS 34DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9846387 secRG 181DW 60.800 usecDE 6.00 usecTE 296.7 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 11.42 usecPL1 -3.00 dBSFO1 400.1324710 MHz
F2 - Processing parametersSI 32768SF 400.1299970 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00
180 160 140 120 100 80 60 40 20 ppm
38.89
39.10
39.31
39.52
39.73
39.93
40.14
119.75
126.38
126.76
126.93
127.42
128.49
129.83
130.03
130.79
131.42
132.13
135.58
139.98
141.64
160.70
167.84
Current Data ParametersNAME MMA-II-399-3EXPNO 4PROCNO 1
F2 - Acquisition ParametersDate_ 20141117Time 14.22INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zgpg30TD 65536SOLVENT DMSONS 1394DS 4SWH 24038.461 HzFIDRES 0.366798 HzAQ 1.3631988 secRG 71.8DW 20.800 usecDE 6.00 usecTE 297.4 KD1 2.00000000 secd11 0.03000000 secDELTA 1.89999998 secTD0 1
======== CHANNEL f1 ========NUC1 13CP1 9.15 usecPL1 0.00 dBSFO1 100.6228298 MHz
======== CHANNEL f2 ========CPDPRG2 waltz16NUC2 1HPCPD2 90.00 usecPL12 14.90 dBPL13 14.90 dBPL2 -3.00 dBSFO2 400.1316005 MHz
F2 - Processing parametersSI 32768SF 100.6128132 MHzWDW EMSSB 0LB 1.00 HzGB 0PC 1.40
C13CPD DMSO {D:\CRR} KOPAL 1
11 10 9 8 7 6 5 4 3 2 1 ppm2.49
02.49
72.50
12.50
62.51
0
3.59
23.62
43.90
1
6.95
07.20
77.21
57.22
17.22
97.29
27.40
77.41
57.42
07.42
87.50
97.52
37.86
47.87
27.87
87.88
68.23
68.25
18.36
0
3.02
2.95
1.00
1.14
1.07
2.06
1.06
1.16
0.97
Current Data ParametersNAME MMA-II-492EXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20150803Time 11.48INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zg30TD 65536SOLVENT DMSONS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9846387 secRG 128DW 60.800 usecDE 6.00 usecTE 297.3 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 11.42 usecPL1 -3.00 dBSFO1 400.1324710 MHz
F2 - Processing parametersSI 32768SF 400.1299969 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00
PROTON DMSO {D:\CRR} KOPAL 1
Figure S9- 1H and 13C NMR spectra of compound (2a)Figure S10- 1H and 13C NMR spectra of compound (2b)
Figure S11- 1H and 13C NMR spectra of compound (2c)
180 160 140 120 100 80 60 40 20 ppm
38.89
39.10
39.31
39.52
39.73
39.93
40.14
55.79
56.00
107.03
108.37
113.18
119.39
126.82
128.72
129.09
129.52
130.02
130.66
137.28
141.53
145.80
147.87
149.83
167.70
Current Data ParametersNAME MK-22-2,5-OMeEXPNO 2PROCNO 1
F2 - Acquisition ParametersDate_ 20160813Time 12.44INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zgpg30TD 65536SOLVENT DMSONS 256DS 4SWH 24038.461 HzFIDRES 0.366798 HzAQ 1.3631988 secRG 71.8DW 20.800 usecDE 6.00 usecTE 292.3 KD1 2.00000000 secd11 0.03000000 secDELTA 1.89999998 secTD0 1
======== CHANNEL f1 ========NUC1 13CP1 9.15 usecPL1 0.00 dBSFO1 100.6228298 MHz
======== CHANNEL f2 ========CPDPRG2 waltz16NUC2 1HPCPD2 90.00 usecPL12 14.90 dBPL13 14.90 dBPL2 -3.00 dBSFO2 400.1316005 MHz
F2 - Processing parametersSI 32768SF 100.6128062 MHzWDW EMSSB 0LB 1.00 HzGB 0PC 1.40
C13CPD DMSO {D:\CRR} KOPAL 1
11 10 9 8 7 6 5 4 3 2 1 0 ppm
2.491
2.496
2.500
2.505
2.509
3.338
3.405
3.946
6.859
6.881
7.094
7.116
7.176
7.179
7.195
7.197
7.450
7.453
7.468
7.472
7.487
7.491
7.537
7.540
7.555
7.559
7.574
7.577
7.895
7.910
7.915
7.932
7.935
8.309
8.440
8.454
3.19
3.03
0.98
1.01
1.01
0.99
1.05
2.01
1.00
PROTON DMSO {D:\CRR} KOPAL 1Current Data ParametersNAME MK-22-2,5-OMeEXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20160813Time 12.31INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zg30TD 65536SOLVENT DMSONS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9846387 secRG 128DW 60.800 usecDE 6.00 usecTE 291.5 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 11.42 usecPL1 -3.00 dBSFO1 400.1324710 MHz
F2 - Processing parametersSI 32768SF 400.1299968 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00
180 160 140 120 100 80 60 40 20 ppm
55.62
55.76
76.84
77.16
77.48
97.83
100.27
115.92
119.59
124.31
127.46
129.39
130.01
130.18
130.49
132.37
140.31
152.72
158.69
159.44
162.79
Current Data ParametersNAME MMA-II-393-2EXPNO 5PROCNO 1
F2 - Acquisition ParametersDate_ 20141104Time 16.49INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zgpg30TD 65536SOLVENT CDCl3NS 1024DS 4SWH 24038.461 HzFIDRES 0.366798 HzAQ 1.3631988 secRG 36DW 20.800 usecDE 6.00 usecTE 297.9 KD1 2.00000000 secd11 0.03000000 secDELTA 1.89999998 secTD0 1
======== CHANNEL f1 ========NUC1 13CP1 9.15 usecPL1 0.00 dBSFO1 100.6228298 MHz
======== CHANNEL f2 ========CPDPRG2 waltz16NUC2 1HPCPD2 90.00 usecPL12 14.90 dBPL13 14.90 dBPL2 -3.00 dBSFO2 400.1316005 MHz
F2 - Processing parametersSI 32768SF 100.6127537 MHzWDW EMSSB 0LB 1.00 HzGB 0PC 1.40
C13CPD CDCl3 {D:\CRR} KOPAL 1
10 9 8 7 6 5 4 3 2 1 ppm1.98
72.17
0
2.59
7
3.41
5
3.93
0
6.41
86.42
36.71
46.72
07.18
17.20
07.40
47.42
27.43
97.46
57.47
77.49
27.49
57.51
17.51
97.98
78.00
58.26
98.28
2
3.17
3.00
1.07
1.03
1.09
1.11
2.12
1.11
1.00
Current Data ParametersNAME MMA-II-393-2EXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20141104Time 11.21INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zg30TD 65536SOLVENT CDCl3NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9846387 secRG 322DW 60.800 usecDE 6.00 usecTE 296.5 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 11.42 usecPL1 -3.00 dBSFO1 400.1324710 MHz
F2 - Processing parametersSI 32768SF 400.1300051 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00
PROTON CDCl3 {D:\CRR} KOPAL 1
Figure S12- 1H and 13C NMR spectra of compound (2d)
Figure S13- 1H and 13C NMR spectra of compound (2e)
Figure S14- 1H NMR spectra of compound (2f)
Figure S15- 1H NMR spectra of compound (2g)
10 9 8 7 6 5 4 3 2 1 0 ppm
1.771
2.501
3.565
6.492
6.579
6.642
6.665
6.692
6.713
6.729
6.750
6.797
6.819
6.885
6.972
6.992
7.050
7.108
7.154
7.259
7.279
7.356
7.368
7.387
7.420
7.429
7.438
7.558
7.572
7.623
7.665
7.915
7.930
7.981
8.001
8.047
2.71
0.72
1.23
3.36
1.45
1.00
1.75
PROTON DMSO {D:\CRR} KOPAL 1Current Data ParametersNAME MMA-II-491EXPNO 2PROCNO 1
F2 - Acquisition ParametersDate_ 20150731Time 12.45INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zg30TD 65536SOLVENT DMSONS 64DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9846387 secRG 161DW 60.800 usecDE 6.00 usecTE 295.3 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 11.42 usecPL1 -3.00 dBSFO1 400.1324710 MHz
F2 - Processing parametersSI 32768SF 400.1299969 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00
10 9 8 7 6 5 4 3 2 1 0 ppm
2.496
2.500
2.504
3.838
3.866
3.869
3.961
6.719
6.755
6.804
6.836
7.174
7.189
7.195
7.401
7.485
7.497
7.640
7.654
7.851
7.873
7.886
7.895
8.134
8.146
8.279
8.294
8.324
8.358
3.12
2.61
2.85
1.17
1.12
3.00
1.25
1.17
PROTON CDCl3 D:CRR KOPAL 1Current Data ParametersNAME MMA-II-498EXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20150812Time 12.37INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zg30TD 65536SOLVENT DMSONS 64DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9846387 secRG 144DW 60.800 usecDE 6.00 usecTE 295.8 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 11.42 usecPL1 -3.00 dBSFO1 400.1324710 MHz
F2 - Processing parametersSI 32768SF 400.1318993 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00
Figure S13- 1H and 13C NMR spectra of compound (2e)
10 9 8 7 6 5 4 3 2 1 ppm
2.500
3.475
3.834
6.900
6.906
7.160
7.166
7.181
7.188
7.530
7.536
7.542
7.710
7.716
7.722
7.730
7.737
7.743
7.750
7.790
7.804
7.983
8.005
8.027
8.460
8.475
3.14
1.01
1.06
2.04
1.04
1.07
2.02
1.00
Current Data ParametersNAME MK-84-iEXPNO 4PROCNO 1
F2 - Acquisition ParametersDate_ 20161225Time 16.27INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zg30TD 65536SOLVENT DMSONS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9846387 secRG 90.5DW 60.800 usecDE 6.00 usecTE 293.9 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 11.42 usecPL1 -3.00 dBSFO1 400.1324710 MHz
F2 - Processing parametersSI 32768SF 400.1299969 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00
PROTON DMSO {D:\CRR} KOPAL 1
180 160 140 120 100 80 60 40 20 ppm
38.89
39.10
39.31
39.52
39.73
39.94
40.15
55.76
113.97
116.11
119.90
123.68
126.46
126.98
127.52
130.13
132.45
135.55
141.65
142.66
160.92
161.72
167.08
Current Data ParametersNAME MK-84-iEXPNO 5PROCNO 1
F2 - Acquisition ParametersDate_ 20161225Time 17.18INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zgpg30TD 65536SOLVENT DMSONS 512DS 4SWH 24038.461 HzFIDRES 0.366798 HzAQ 1.3631988 secRG 80.6DW 20.800 usecDE 6.00 usecTE 294.1 KD1 2.00000000 secd11 0.03000000 secDELTA 1.89999998 secTD0 1
======== CHANNEL f1 ========NUC1 13CP1 9.15 usecPL1 0.00 dBSFO1 100.6228298 MHz
======== CHANNEL f2 ========CPDPRG2 waltz16NUC2 1HPCPD2 90.00 usecPL12 14.90 dBPL13 14.90 dBPL2 -3.00 dBSFO2 400.1316005 MHz
F2 - Processing parametersSI 32768SF 100.6128002 MHzWDW EMSSB 0LB 1.00 HzGB 0PC 1.40
C13CPD DMSO {D:\CRR} KOPAL 1
11 10 9 8 7 6 5 4 3 2 1 0 ppm2.495
2.500
2.504
2.507
2.511
3.845
6.902
6.920
7.129
7.147
7.168
7.421
7.439
7.458
7.465
7.483
7.501
7.519
7.538
7.589
7.611
7.789
7.802
7.840
7.862
7.935
7.955
8.012
8.025
8.047
8.168
8.511
8.524
0.87
0.91
3.00
1.11
0.90
1.14
1.02
1.90
0.86
PROTON DMSO {D:\CRR} KOPAL 1Current Data ParametersNAME MK-28-NAPTHYLEXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20160717Time 12.40INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zg30TD 65536SOLVENT DMSONS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9846387 secRG 32DW 60.800 usecDE 6.00 usecTE 296.3 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 11.42 usecPL1 -3.00 dBSFO1 400.1324710 MHz
F2 - Processing parametersSI 32768SF 400.1299971 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00
180 160 140 120 100 80 60 40 20 ppm
38.90
39.11
39.31
39.52
39.73
39.94
40.15
120.64
123.92
126.17
126.78
127.16
127.56
128.24
129.30
129.75
130.84
130.93
132.14
133.49
133.88
136.31
137.62
143.20
144.79
160.99
170.46
Current Data ParametersNAME MK-28-NAPTHYLEXPNO 3PROCNO 1
F2 - Acquisition ParametersDate_ 20160718Time 21.03INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zgpg30TD 65536SOLVENT DMSONS 3000DS 4SWH 24038.461 HzFIDRES 0.366798 HzAQ 1.3631988 secRG 114DW 20.800 usecDE 6.00 usecTE 295.0 KD1 2.00000000 secd11 0.03000000 secDELTA 1.89999998 secTD0 1
======== CHANNEL f1 ========NUC1 13CP1 9.15 usecPL1 0.00 dBSFO1 100.6228298 MHz
======== CHANNEL f2 ========CPDPRG2 waltz16NUC2 1HPCPD2 90.00 usecPL12 14.90 dBPL13 14.90 dBPL2 -3.00 dBSFO2 400.1316005 MHz
F2 - Processing parametersSI 32768SF 100.6127567 MHzWDW EMSSB 0LB 1.00 HzGB 0PC 1.40
C13CPD DMSO {D:\CRR} KOPAL 1Figure S16- 1H and 13C NMR spectra of compound (2h)
Figure S17- 1H and 13C NMR spectra of compound (2i)
180 160 140 120 100 80 60 40 20 ppm
51.78
55.73
76.84
77.16
77.47
114.45
115.90
120.16
122.68
126.88
127.00
127.31
127.58
130.09
132.81
136.03
141.88
143.28
161.31
162.58
166.54
Current Data ParametersNAME MK-85EXPNO 3PROCNO 1
F2 - Acquisition ParametersDate_ 20161225Time 10.33INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zgpg30TD 65536SOLVENT CDCl3NS 512DS 4SWH 24038.461 HzFIDRES 0.366798 HzAQ 1.3631988 secRG 32DW 20.800 usecDE 6.00 usecTE 294.0 KD1 2.00000000 secd11 0.03000000 secDELTA 1.89999998 secTD0 1
======== CHANNEL f1 ========NUC1 13CP1 9.15 usecPL1 0.00 dBSFO1 100.6228298 MHz
======== CHANNEL f2 ========CPDPRG2 waltz16NUC2 1HPCPD2 90.00 usecPL12 14.90 dBPL13 14.90 dBPL2 -3.00 dBSFO2 400.1316005 MHz
F2 - Processing parametersSI 32768SF 100.6127555 MHzWDW EMSSB 0LB 1.00 HzGB 0PC 1.40
C13CPD CDCl3 {D:\CRR} KOPAL 1
11 10 9 8 7 6 5 4 3 2 1 0 ppm3.399
3.871
6.961
6.967
7.049
7.056
7.071
7.078
7.260
7.436
7.439
7.453
7.457
7.460
7.474
7.477
7.583
7.585
7.604
7.606
7.638
7.641
7.655
7.658
7.661
7.667
7.676
7.680
7.864
7.885
8.106
8.128
8.552
8.567
2.85
2.86
0.90
0.92
1.17
1.08
2.21
1.06
0.85
1.00
Current Data ParametersNAME MK-85EXPNO 2PROCNO 1
F2 - Acquisition ParametersDate_ 20161224Time 11.27INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zg30TD 65536SOLVENT CDCl3NS 32DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9846387 secRG 228DW 60.800 usecDE 6.00 usecTE 293.6 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 11.42 usecPL1 -3.00 dBSFO1 400.1324710 MHz
F2 - Processing parametersSI 32768SF 400.1300050 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00
PROTON CDCl3 {D:\CRR} KOPAL 1
11 10 9 8 7 6 5 4 3 2 1 0 ppm
3.396
3.428
3.979
6.683
6.704
6.888
6.909
7.260
7.309
7.311
7.327
7.330
7.420
7.423
7.439
7.442
7.458
7.461
7.542
7.545
7.560
7.564
7.579
7.582
8.020
8.035
8.039
8.056
8.059
8.554
8.569
3.01
3.00
3.02
1.09
1.07
1.04
1.07
1.07
2.09
1.04
Current Data ParametersNAME MK-74-IVEXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20161125Time 17.36INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zg30TD 65536SOLVENT CDCl3NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9846387 secRG 228DW 60.800 usecDE 6.00 usecTE 292.9 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 11.42 usecPL1 -3.00 dBSFO1 400.1324710 MHz
F2 - Processing parametersSI 32768SF 400.1300051 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00
PROTON CDCl3 {D:\CRR} KOPAL 1
180 160 140 120 100 80 60 40 20 ppm
51.74
55.87
56.01
76.84
77.16
77.48
106.40
107.72
114.06
120.17
127.06
129.13
129.33
129.51
130.17
131.44
141.83
146.08
148.74
150.33
158.63
167.35
Current Data ParametersNAME MK-74-IVEXPNO 2PROCNO 1
F2 - Acquisition ParametersDate_ 20161126Time 17.29INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zgpg30TD 65536SOLVENT CDCl3NS 512DS 4SWH 24038.461 HzFIDRES 0.366798 HzAQ 1.3631988 secRG 28.5DW 20.800 usecDE 6.00 usecTE 292.4 KD1 2.00000000 secd11 0.03000000 secDELTA 1.89999998 secTD0 1
======== CHANNEL f1 ========NUC1 13CP1 9.15 usecPL1 0.00 dBSFO1 100.6228298 MHz
======== CHANNEL f2 ========CPDPRG2 waltz16NUC2 1HPCPD2 90.00 usecPL12 14.90 dBPL13 14.90 dBPL2 -3.00 dBSFO2 400.1316005 MHz
F2 - Processing parametersSI 32768SF 100.6127567 MHzWDW EMSSB 0LB 1.00 HzGB 0PC 1.40
C13CPD CDCl3 {D:\CRR} KOPAL 1
10 9 8 7 6 5 4 3 2 1 0 ppm
-0.001
2.067
3.440
3.774
4.040
6.867
7.127
7.260
7.521
7.535
7.545
7.548
7.557
7.564
7.568
7.583
7.587
7.650
7.653
7.669
7.672
7.688
7.691
8.065
8.068
8.085
8.441
8.455
3.04
3.03
3.19
0.98
1.02
3.21
1.08
1.00
1.00
PROTON CDCl3 {D:\CRR} KOPAL 1Current Data ParametersNAME MMA-II-391EXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20141031Time 13.07INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zg30TD 65536SOLVENT CDCl3NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9846387 secRG 287DW 60.800 usecDE 6.00 usecTE 296.7 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 11.42 usecPL1 -3.00 dBSFO1 400.1324710 MHz
F2 - Processing parametersSI 32768SF 400.1300051 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00
180 160 140 120 100 80 60 40 20 ppm
52.09
55.94
56.20
76.84
77.16
77.48
104.83
105.15
119.05
123.27
128.61
130.46
130.96
131.11
132.12
133.12
140.69
140.92
150.22
152.80
158.35
167.62
Current Data ParametersNAME MMA-II-391EXPNO 2PROCNO 1
F2 - Acquisition ParametersDate_ 20141101Time 13.58INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zgpg30TD 65536SOLVENT CDCl3NS 1024DS 4SWH 24038.461 HzFIDRES 0.366798 HzAQ 1.3631988 secRG 64DW 20.800 usecDE 6.00 usecTE 295.7 KD1 2.00000000 secd11 0.03000000 secDELTA 1.89999998 secTD0 1
======== CHANNEL f1 ========NUC1 13CP1 9.15 usecPL1 0.00 dBSFO1 100.6228298 MHz
======== CHANNEL f2 ========CPDPRG2 waltz16NUC2 1HPCPD2 90.00 usecPL12 14.90 dBPL13 14.90 dBPL2 -3.00 dBSFO2 400.1316005 MHz
F2 - Processing parametersSI 32768SF 100.6127559 MHzWDW EMSSB 0LB 1.00 HzGB 0PC 1.40
C13CPD CDCl3 {D:\CRR} KOPAL 1
12 11 10 9 8 7 6 5 4 3 2 1 0 ppm
0.000
3.419
7.260
7.441
7.444
7.458
7.462
7.465
7.479
7.482
7.494
7.496
7.512
7.515
7.552
7.555
7.571
7.574
7.590
7.593
7.612
7.634
7.638
7.642
7.646
7.661
7.676
7.865
7.886
8.106
8.109
8.126
8.129
8.559
8.573
3.32
0.72
1.37
1.07
4.14
1.12
1.03
1.00
PROTON CDCl3 {D:\CRR} KOPAL 1Current Data ParametersNAME MMA-II-410-1EXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20141201Time 11.36INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zg30TD 65536SOLVENT CDCl3NS 32DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9846387 secRG 114DW 60.800 usecDE 6.00 usecTE 295.4 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 11.42 usecPL1 -3.00 dBSFO1 400.1324710 MHz
F2 - Processing parametersSI 32768SF 400.1300050 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00
180 160 140 120 100 80 60 40 20 ppm
51.99
76.84
77.16
77.48
120.10
126.86
127.02
127.30
127.56
128.63
130.07
130.54
130.85
130.98
132.07
136.13
140.80
141.89
161.14
167.24
Current Data ParametersNAME MMA-II-410-1EXPNO 2PROCNO 1
F2 - Acquisition ParametersDate_ 20141201Time 13.05INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zgpg30TD 65536SOLVENT CDCl3NS 203DS 4SWH 24038.461 HzFIDRES 0.366798 HzAQ 1.3631988 secRG 32DW 20.800 usecDE 6.00 usecTE 296.9 KD1 2.00000000 secd11 0.03000000 secDELTA 1.89999998 secTD0 1
======== CHANNEL f1 ========NUC1 13CP1 9.15 usecPL1 0.00 dBSFO1 100.6228298 MHz
======== CHANNEL f2 ========CPDPRG2 waltz16NUC2 1HPCPD2 90.00 usecPL12 14.90 dBPL13 14.90 dBPL2 -3.00 dBSFO2 400.1316005 MHz
F2 - Processing parametersSI 32768SF 100.6127583 MHzWDW EMSSB 0LB 1.00 HzGB 0PC 1.40
C13CPD CDCl3 {D:\CRR} KOPAL 1
Figure S18- 1H and 13C NMR spectra of compound (4a)
Figure S19- 1H and 13C NMR spectra of compound (4c)
Figure S20- 1H and 13C NMR spectra of compound (4e)
Figure S21- 1H and 13C NMR spectra of compound (4h)
Figure S22- 1H and 13C NMR spectra of compound (A)
12 11 10 9 8 7 6 5 4 3 2 1 ppm
1.58
2
2.10
0
4.12
2
7.26
07.34
97.67
17.68
57.72
37.72
77.74
47.76
17.76
47.90
37.90
67.92
37.92
67.94
17.94
58.56
18.56
38.58
18.58
48.80
88.82
19.08
69.10
6
3.03
0.96
0.98
1.07
1.01
0.99
1.00
1.00
Current Data ParametersNAME MK-77-IIEXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20161124Time 16.37INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zg30TD 65536SOLVENT CDCl3NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9846387 secRG 287DW 60.800 usecDE 6.00 usecTE 293.2 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 11.42 usecPL1 -3.00 dBSFO1 400.1324710 MHz
F2 - Processing parametersSI 32768SF 400.1300051 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00
PROTON CDCl3 {D:\CRR} KOPAL 1
16.1 ppm
16.0
550.90
11 10 9 8 7 6 5 4 3 2 1 ppm
7.260
7.634
7.637
7.654
7.655
7.672
7.675
7.740
7.754
7.794
7.797
7.814
7.815
7.817
7.832
7.835
7.889
7.908
7.910
7.928
8.141
8.143
8.161
8.164
8.408
8.411
8.428
8.431
8.652
8.655
8.670
8.673
8.770
8.784
1.00
0.99
1.02
1.01
0.99
0.97
0.98
0.98
1.00
Current Data ParametersNAME MK-68-IEXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20161109Time 16.02INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zg30TD 65536SOLVENT CDCl3NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9846387 secRG 228DW 60.800 usecDE 6.00 usecTE 293.3 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 11.42 usecPL1 -3.00 dBSFO1 400.1324710 MHz
F2 - Processing parametersSI 32768SF 400.1300051 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00
PROTON CDCl3 {D:\CRR} KOPAL 1
180 160 140 120 100 80 60 40 20 ppm
76.84
77.16
77.48
121.00
122.96
125.39
127.66
129.15
129.97
130.48
130.62
132.44
133.48
134.13
135.22
136.83
144.12
148.81
183.45
Current Data ParametersNAME MK-68EXPNO 2PROCNO 1
F2 - Acquisition ParametersDate_ 20161109Time 12.01INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zgpg30TD 65536SOLVENT CDCl3NS 153DS 4SWH 24038.461 HzFIDRES 0.366798 HzAQ 1.3631988 secRG 28.5DW 20.800 usecDE 6.00 usecTE 293.8 KD1 2.00000000 secd11 0.03000000 secDELTA 1.89999998 secTD0 1
======== CHANNEL f1 ========NUC1 13CP1 9.15 usecPL1 0.00 dBSFO1 100.6228298 MHz
======== CHANNEL f2 ========CPDPRG2 waltz16NUC2 1HPCPD2 90.00 usecPL12 14.90 dBPL13 14.90 dBPL2 -3.00 dBSFO2 400.1316005 MHz
F2 - Processing parametersSI 32768SF 100.6127564 MHzWDW EMSSB 0LB 1.00 HzGB 0PC 1.40
C13CPD CDCl3 {D:\CRR} KOPAL 1
11 10 9 8 7 6 5 4 3 2 1 ppm
0.068
1.248
1.597
7.260
7.643
7.646
7.663
7.680
7.683
7.784
7.787
7.805
7.822
7.825
7.982
8.001
8.003
8.021
8.377
8.379
8.396
8.398
8.459
8.462
8.480
8.482
8.694
8.696
8.712
8.714
8.822
8.842
8.909
1.07
1.10
1.09
1.07
1.00
1.06
1.03
0.99
Current Data ParametersNAME MK-76-IEXPNO 1PROCNO 1
F2 - Acquisition ParametersDate_ 20161116Time 15.36INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zg30TD 65536SOLVENT CDCl3NS 16DS 2SWH 8223.685 HzFIDRES 0.125483 HzAQ 3.9846387 secRG 256DW 60.800 usecDE 6.00 usecTE 293.3 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 11.42 usecPL1 -3.00 dBSFO1 400.1324710 MHz
F2 - Processing parametersSI 32768SF 400.1300051 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00
PROTON CDCl3 {D:\CRR} KOPAL 1
180 160 140 120 100 80 60 40 20 ppm
76.85
77.16
77.48
116.18
117.36
120.27
125.57
127.81
129.43
130.86
131.70
132.08
132.70
134.30
134.40
136.38
145.86
148.17
183.06
Current Data ParametersNAME MK-76-IEXPNO 5PROCNO 1
F2 - Acquisition ParametersDate_ 20161119Time 11.09INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zgpg30TD 65536SOLVENT CDCl3NS 512DS 4SWH 24038.461 HzFIDRES 0.366798 HzAQ 1.3631988 secRG 28.5DW 20.800 usecDE 6.00 usecTE 293.5 KD1 2.00000000 secd11 0.03000000 secDELTA 1.89999998 secTD0 1
======== CHANNEL f1 ========NUC1 13CP1 9.15 usecPL1 0.00 dBSFO1 100.6228298 MHz
======== CHANNEL f2 ========CPDPRG2 waltz16NUC2 1HPCPD2 90.00 usecPL12 14.90 dBPL13 14.90 dBPL2 -3.00 dBSFO2 400.1316005 MHz
F2 - Processing parametersSI 32768SF 100.6127541 MHzWDW EMSSB 0LB 1.00 HzGB 0PC 1.40
C13CPD CDCl3 {D:\CRR} KOPAL 1
Figure S22- 1H and 13C NMR spectra of compound (A)
Figure S23- 1H and 13C NMR spectra of compound (B)
5060708090100110120130140150160170180 ppm
56.53
76.85
77.17
77.49
108.79
112.15
114.23
120.69
125.41
126.62
129.69
130.47
131.08
134.28
139.46
143.75
144.24
153.18
164.73
185.17
Current Data ParametersNAME MK-77-FEXPNO 2PROCNO 1
F2 - Acquisition ParametersDate_ 20161223Time 9.50INSTRUM spectPROBHD 5 mm DUL 13C-1PULPROG zgpg30TD 65536SOLVENT CDCl3NS 17000DS 4SWH 24038.461 HzFIDRES 0.366798 HzAQ 1.3631988 secRG 28.5DW 20.800 usecDE 6.00 usecTE 293.9 KD1 2.00000000 secd11 0.03000000 secDELTA 1.89999998 secTD0 1
======== CHANNEL f1 ========NUC1 13CP1 9.15 usecPL1 0.00 dBSFO1 100.6228298 MHz
======== CHANNEL f2 ========CPDPRG2 waltz16NUC2 1HPCPD2 90.00 usecPL12 14.90 dBPL13 14.90 dBPL2 -3.00 dBSFO2 400.1316005 MHz
F2 - Processing parametersSI 32768SF 100.6127531 MHzWDW EMSSB 0LB 1.00 HzGB 0PC 1.40
C13CPD CDCl3 {D:\CRR} KOPAL 1
Figure S24- 1H and 13C NMR spectra of compound (C)