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S1 Supporting Information Transition metal-free one-pot cascade synthesis of 7-oxa-2- azatricyclo[7.4.0.0 2,6 ]trideca-1(9),10,12-trien-3-ones from biomass- derived levulinic acid under mild conditions Amitabh Jha,* Ajay B. Naidu, Ashraf M. Abdelkhalik Department of Chemistry, Acadia University, Wolfville, Nova Scotia, B4P2R6, Canada [email protected] Table of Contents for Supporting Information 1. 1 H and 13 C NMR spectra of 1a-1i S2 2. 1 H and 13 C NMR spectra of 1a’-1i’ S11 3. 1 H and 13 C NMR spectra of 2a, 2b, 2c, 3a and 3b S20 Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is © The Royal Society of Chemistry 2013

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Page 1: Supporting Information Transition metal-free one-pot …Amitabh Jha,* Ajay B. Naidu, Ashraf M. Abdelkhalik Department of Chemistry, Acadia University, Wolfville, Nova Scotia, B4P2R6,

S1

Supporting Information

Transition metal-free one-pot cascade synthesis of 7-oxa-2-azatricyclo[7.4.0.02,6]trideca-1(9),10,12-trien-3-ones from biomass-

derived levulinic acid under mild conditions Amitabh Jha,* Ajay B. Naidu, Ashraf M. Abdelkhalik

Department of Chemistry, Acadia University, Wolfville, Nova Scotia, B4P2R6, Canada

[email protected]

Table of Contents for Supporting Information

1. 1H and 13C NMR spectra of 1a-1i S2 2. 1H and 13C NMR spectra of 1a’-1i’ S11 3. 1H and 13C NMR spectra of 2a, 2b, 2c, 3a and 3b S20

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013

mailto:[email protected]
Page 2: Supporting Information Transition metal-free one-pot …Amitabh Jha,* Ajay B. Naidu, Ashraf M. Abdelkhalik Department of Chemistry, Acadia University, Wolfville, Nova Scotia, B4P2R6,

S2

1H and 13C NMR spectra of 1a-1i

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013

Page 3: Supporting Information Transition metal-free one-pot …Amitabh Jha,* Ajay B. Naidu, Ashraf M. Abdelkhalik Department of Chemistry, Acadia University, Wolfville, Nova Scotia, B4P2R6,

S3

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013

Page 4: Supporting Information Transition metal-free one-pot …Amitabh Jha,* Ajay B. Naidu, Ashraf M. Abdelkhalik Department of Chemistry, Acadia University, Wolfville, Nova Scotia, B4P2R6,

S4

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013

Page 5: Supporting Information Transition metal-free one-pot …Amitabh Jha,* Ajay B. Naidu, Ashraf M. Abdelkhalik Department of Chemistry, Acadia University, Wolfville, Nova Scotia, B4P2R6,

S5

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013

Page 6: Supporting Information Transition metal-free one-pot …Amitabh Jha,* Ajay B. Naidu, Ashraf M. Abdelkhalik Department of Chemistry, Acadia University, Wolfville, Nova Scotia, B4P2R6,

S6

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013

Page 7: Supporting Information Transition metal-free one-pot …Amitabh Jha,* Ajay B. Naidu, Ashraf M. Abdelkhalik Department of Chemistry, Acadia University, Wolfville, Nova Scotia, B4P2R6,

S7

N

O

O

I

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013

Page 8: Supporting Information Transition metal-free one-pot …Amitabh Jha,* Ajay B. Naidu, Ashraf M. Abdelkhalik Department of Chemistry, Acadia University, Wolfville, Nova Scotia, B4P2R6,

S8

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013

Page 9: Supporting Information Transition metal-free one-pot …Amitabh Jha,* Ajay B. Naidu, Ashraf M. Abdelkhalik Department of Chemistry, Acadia University, Wolfville, Nova Scotia, B4P2R6,

S9

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013

Page 10: Supporting Information Transition metal-free one-pot …Amitabh Jha,* Ajay B. Naidu, Ashraf M. Abdelkhalik Department of Chemistry, Acadia University, Wolfville, Nova Scotia, B4P2R6,

S10

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013

Page 11: Supporting Information Transition metal-free one-pot …Amitabh Jha,* Ajay B. Naidu, Ashraf M. Abdelkhalik Department of Chemistry, Acadia University, Wolfville, Nova Scotia, B4P2R6,

S11

1H and 13C NMR spectra of 1a’-1i’

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013

Page 12: Supporting Information Transition metal-free one-pot …Amitabh Jha,* Ajay B. Naidu, Ashraf M. Abdelkhalik Department of Chemistry, Acadia University, Wolfville, Nova Scotia, B4P2R6,

S12

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013

Page 13: Supporting Information Transition metal-free one-pot …Amitabh Jha,* Ajay B. Naidu, Ashraf M. Abdelkhalik Department of Chemistry, Acadia University, Wolfville, Nova Scotia, B4P2R6,

S13

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013

Page 14: Supporting Information Transition metal-free one-pot …Amitabh Jha,* Ajay B. Naidu, Ashraf M. Abdelkhalik Department of Chemistry, Acadia University, Wolfville, Nova Scotia, B4P2R6,

S14

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013

Page 15: Supporting Information Transition metal-free one-pot …Amitabh Jha,* Ajay B. Naidu, Ashraf M. Abdelkhalik Department of Chemistry, Acadia University, Wolfville, Nova Scotia, B4P2R6,

S15

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013

Page 16: Supporting Information Transition metal-free one-pot …Amitabh Jha,* Ajay B. Naidu, Ashraf M. Abdelkhalik Department of Chemistry, Acadia University, Wolfville, Nova Scotia, B4P2R6,

S16

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013

Page 17: Supporting Information Transition metal-free one-pot …Amitabh Jha,* Ajay B. Naidu, Ashraf M. Abdelkhalik Department of Chemistry, Acadia University, Wolfville, Nova Scotia, B4P2R6,

S17

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013

Page 18: Supporting Information Transition metal-free one-pot …Amitabh Jha,* Ajay B. Naidu, Ashraf M. Abdelkhalik Department of Chemistry, Acadia University, Wolfville, Nova Scotia, B4P2R6,

S18

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013

Page 19: Supporting Information Transition metal-free one-pot …Amitabh Jha,* Ajay B. Naidu, Ashraf M. Abdelkhalik Department of Chemistry, Acadia University, Wolfville, Nova Scotia, B4P2R6,

S19

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013

Page 20: Supporting Information Transition metal-free one-pot …Amitabh Jha,* Ajay B. Naidu, Ashraf M. Abdelkhalik Department of Chemistry, Acadia University, Wolfville, Nova Scotia, B4P2R6,

S20

1H and 13C NMR spectra of 2a, 2b, 2c, 3a and 3b

1.0001.1412.3421.1611.0641.992 1.0611.025 3.089

PPM 8.8 8.4 8.0 7.6 7.2 6.8 6.4 6.0 5.6 5.2 4.8 4.4 4.0 3.6 3.2 2.8 2.4 2.0 1.6 1.2 0.8 0.4 0.0

8.15658.14067.82877.82737.81377.69517.68147.66647.65437.65227.64937.64267.64137.62877.62767.62617.58117.57837.56607.56377.55217.54937.34177.33447.32947.32597.31877.31317.15857.15657.14617.1448 5.38205.37925.20345.17224.96284.9316 1.71951.7168

PPM 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20

19.651961.949886.9751120.1456121.0554121.9466122.8464123.2400123.4008126.5018129.0887129.8921131.4060132.1679145.0036163.7866

N

O

O

N

O

O

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013

Page 21: Supporting Information Transition metal-free one-pot …Amitabh Jha,* Ajay B. Naidu, Ashraf M. Abdelkhalik Department of Chemistry, Acadia University, Wolfville, Nova Scotia, B4P2R6,

S21

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013

Page 22: Supporting Information Transition metal-free one-pot …Amitabh Jha,* Ajay B. Naidu, Ashraf M. Abdelkhalik Department of Chemistry, Acadia University, Wolfville, Nova Scotia, B4P2R6,

S22

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013

Page 23: Supporting Information Transition metal-free one-pot …Amitabh Jha,* Ajay B. Naidu, Ashraf M. Abdelkhalik Department of Chemistry, Acadia University, Wolfville, Nova Scotia, B4P2R6,

S23

NH

OH

O4

O

NH

OH

O4

O

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013

Page 24: Supporting Information Transition metal-free one-pot …Amitabh Jha,* Ajay B. Naidu, Ashraf M. Abdelkhalik Department of Chemistry, Acadia University, Wolfville, Nova Scotia, B4P2R6,

S24

1.0000.976 1.1471.0611.008 2.152 2.1892.4023.082 2.3282.6702.3710.808

PPM 8.4 8.0 7.6 7.2 6.8 6.4 6.0 5.6 5.2 4.8 4.4 4.0 3.6 3.2 2.8 2.4 2.0 1.6 1.2 0.8

8.7014 8.07318.05697.36497.36207.34917.34717.33397.33097.29917.22147.20677.11977.1050 4.7227 2.50112.48662.47222.43462.41982.40502.16652.14551.78021.76501.74991.66311.64791.63261.61791.42861.41961.41381.40241.3979

PPM 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20

23.475325.529128.769730.192937.732043.602264.6300122.7085124.4659129.0690129.2580129.8256137.6608171.9134209.6897

NH

OH

O5

O

NH

OH

O5

O

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013


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