catalyst free microwave assisted arylglyoxal based ...catalyst‐free microwave‐assisted...
TRANSCRIPT
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Catalyst‐free microwave‐assisted arylglyoxal‐based multicomponent reactions for the synthesis of fused pyrans
Richa Mishra and Lokman H. Choudhury*
Department of Chemistry, Indian Institute of Technology Patna, Patna‐801103, Bihar, INDIA
E‐mail: [email protected], [email protected]; Tel: +916123028038
Table of contents
Title page...............................................................................................S1
General experimental information...........................................................S2
Copies of 1H and 13C NMR spectrum of all compounds...........................S3‐S34
S1
Electronic Supplementary Material (ESI) for RSC Advances.This journal is © The Royal Society of Chemistry 2016
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General Experimental Information
All starting materials were purchased from either Sigma Aldrich or Alfa Aesar and used without further purification. Microwave irradiation was
carried out with Initiator 2.5 Microwave Synthesizers from Biotage, Uppsala, Sweden. NMR spectra were recorded on Bruker 400 or 500 MHz
for 1H and 100 or 125 MHz for 13C in CDCl3/DMSO‐d6, chemical shift values were reported in δ values ppm downfield from tetra methyl silane.
Infrared spectra were recorded on a Shimadzu FTIR spectrometer. CHN analyses were carried out using Elementar, Vario micro cube
elemental analyzer and melting points were recorded using SRS EZ‐ Melt automated melting point apparatus by capillary methods and
uncorrected.
Typical experimental procedure for the synthesis of 1(a). Typical experimental procedure for the preparation of 1a: A mixture of
phenylglyoxal monohydrate (1.0 mmol) and malononitrile (1.0 mmol) in ethanol (2 ml) was stirred at room temperature for 5 minutes. To this
mixture 4‐hydroxy‐1‐methyl‐2(1H)‐quinolone (1 mmol) was added and the resultant mixture was kept under microwave irradiation with sealed
and stirring conditions for 10 minutes, keeping the temperature at 110 oC . After completion of the reaction, the reaction mixture was cooled
to room temperature and solid product was separated by just filtration and purified by recrystallization from mixture of ethanol and THF.
Using similar procedure all other products were prepared.
S2
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1H NMR spectra of 1a
S3
N OCH3
O
NH2CN
O
-
13C NMR spectra of 1a
S4
N OCH3
O
NH2CN
O
-
1H NMR spectra of 1b
S5
N OCH3
O
NH2CN
O
OMe
-
13C NMR spectra of 1b
S6
N OCH3
O
NH2CN
O
OMe
-
1H NMR spectra of 1c
S7
N OCH 3
O
NH 2CN
O
F
-
13C NMR Spectra of 1c
S8
N OCH 3
O
NH 2CN
O
F
-
1H NMR spectra of 1d
S9
N OCH3
O
NH2CN
O
NO2
-
13C NMR spectra of 1d
S10
N OCH3
O
NH2CN
O
NO2
-
1H NMR spectra of 1e
S11
N O
CH3
O
NH2CN
O
O
O
-
13C NMR spectra of 1e
S12
N O
CH3
O
NH2CN
O
O
O
-
1H NMR spectra of 1f
S13
N O
CH3
O
NH2CN
O
OMe
-
13C NMR spectra of 1f
S14
N O
CH3
O
NH2CN
O
OMe
-
1H NMR spectra of 2a
S15
O
O
O
O
CN
NH2
-
13C NMR spectra of 2a
S16
O
O
O
O
CN
NH2
-
1H NMR spectra of 2b
S17
O
O
O
O
CN
NH2
OMe
-
13C NMR spectra of 2b
S18
O
O
O
O
CN
NH2
OMe
-
1H NMR spectra of 2c
S19
O
O
O
O
CN
NH2
F
-
13C NMR spectra of 2c
S20
O
O
O
O
CN
NH2
F
-
1H NMR spectra of 2d
S21
O
O
O
O
CN
NH2
OO
-
13C NMR spectra of 2d
S22
O
O
O
O
CN
NH2
OO
-
1H NMR spectra of 2e
S23
O
O
O
O
CN
NH2
OMe
-
13C NMR spectra of 2e s
S24
O
O
O
O
CN
NH2
OMe
-
1H NMR spectra of 3a
S25
O
O
O
NH2CN
O
-
13C NMR spectra of 3a
S26
O
O
O
NH2CN
O
-
1H NMR spectra of 3b
S27
O
O
O
NH2CN
O
OMe
-
13C NMR spectra of 3b
S28
O
O
O
NH2CN
O
OMe
-
1H NMR spectra of 3c
S29
O
O
O
NH2CN
O
F
-
13C NMR spectra of 3c
S30
O
O
O
NH2CN
O
F
-
1H NMR spectra of 3d
S31
O
O
O
NH2CN
O
NO2
-
13C NMR spectra of 3d
S32
O
O
O
NH2CN
O
NO2
-
1H NMR spectra of 3e
S33
O
O
O
NH2CN
O
-
13C NMR spectra of 3e
S34
O
O
O
NH2CN
O