PDF《Supporting Information》

13 C NMR (CDCl3,

75 MHz) δ en ppm : 40,93 (s, C-4). 60,96 (s, C-3). 116,66 (s, CN). 119,52 (s, C-4a). 120,78 (s, C-10). 123,21 (s, C- 10a). 124,82 (s, C-6). 125,97 (s, C-5). 126,82 (s, C-8). 126,94 (s, C-9). 127,80 (C-7). 129,05 (s, C-3'

,5'

). 129,48 (s, C-2'

, 6'

). 133,27 (s, C-4'

), 133,38 (s, C-6a). 142,93 (s, C-1'

). 143,30 (s, C-10b).

159 (s, C-2). FTIR (KBr) cm-1 :

3433 (CH),

3316 (NH2),

2183 (CN),

1650 (NH2). MS (EI) m/z (%):

332 (M+ ),

221 (100). O NH2 CN CH3 Linear formula : C21H16N2O Molecular weight :

312 g/mol O NH2 CN OMe Linear formula : C21H16N2O Molecular weight :

328 g/mol O NH2 CN Cl Linear formula : C20H13ClN2O Molecular weight :

332 g/mol Supplementary Material (ESI) for Green Chemistry This journal is (c) The Royal Society of Chemistry

2010 S6 2-Amino-3-cyano-4-(4-nitrophenyl)-4H- benzo[h]chromene (4e) : Yellow solid, mp = 239-241°C.

1 H NMR (CDCl3 ,

300 MHz) δ en ppm : 4,96 (2H, s, NH2).

5 (1H, s, H-4). 6,95 (1H, d, JHH = 8,4 Hz, H-5). 7,4 (2H, d, JHH = 8,4 Hz, H-2'

, 6'

). 7,52 -7,62 (3H, m, H-6, 8, 9). 7,81 (1H, d, JHH = 7,2 Hz, H-7). 8,17 (2H, d, JHH = 8,7 Hz, H-3'

, 5'

). 8,28 (1H, d, JHH = 8,7 Hz, H-10).

13 C NMR (CDCl3,

75 MHz) δ en ppm : 41,70 (s, C-4). 61,30 (s, C-3). 117,00 (s, CN). 119,2 (s, C-4a). 121,14 (s, C-10). 123,5 (s, C-10a). 124,59 (s, C-3'

, 5'

). 125,50 (s, C-6). 125,89 (s, C-5). 127,39 (s, C-8). 127,75 (s, C-9).128,20 (s, C-7). 129,35 (s, C-2'

, 6'

). 130,74 (s, C-6a). 133,89 (s, C-4'

).

148 (s, C-1'

). 151,73 (C-10b). 159,72 (C-2). FTIR (KBr) cm-1 :

3454 (CH),

3330 (NH2),

2182 (CN),

1614 (NH2). MS (EI) m/z (%):

343 (M+ ),

221 (100). 2-Amino-3-cyano-4-(3-nitrophenyl)-4H- benzo[h]chromene (4f): Yellow solid, mp = 213-215°C.

1 H NMR (CDCl3 ,

300 MHz) δ en ppm : 4,97 (2H, s, NH2 ). 5,03 (1H, s, H-4). 6,96 (1H, d, JHH = 8,4 Hz, H-5).7,49-7,66 (5H, m, H- 6, 8, 9, 4'

, 5'

). 7,82 (1H, d, JHH = 7,5 Hz, H-7). 8,11 (2H, m, H-2'

, 6'

). 8,21 (1H, d, JHH = 7,8 Hz, H-10).

13 C NMR (CDCl3,

75 MHz) δ en ppm : 41,67 (s, C-4). 61,2 (s, C-3). 116,00 (s, CN). 119,63 (s, C-4a). 121,19 (s, C-10). 122,94 (s, C-9). 123,36 (s, C-6). 123,74 (s, C-10a). 125,47 (s, C-2'

). 125,86 (s, C-4'

). 127,36 (s, C- 7). 127,54 (s, C-5).128,15 (s, C-8). 130,21 (s, C-6'

). 133,85 (C-6a). 134,61 (s, C-5'

).

144 (C-1'

). 146,88 (s, C-3'

). 149,05 (s, C-10b). 159,73 (C-2). FTIR (KBr) cm-1 :

3457 (CH),

3350 (NH2),

2180 (CN),

1614 (NH2). MS (EI) m/z (%) :

343 (M+ ),

221 (100). Characterisation of the Kn?venagel condensation product 4'

g 2-(4-Dimethylamino-benzylidene)- malononitrile (4'

g): Orange solid, mp = 180- 182°C.

1 H NMR (CDCl3,

300 MHz) δ en ppm: 2,89 (6H, s, C6H4N(CH3)2 ). 7,50-7,69 (4H, m, Ph). 7,76 (1H, s, PhCH=C).

13 C NMR (CDCl3,

75 MHz) δ en ppm : 41,6 (6H, s, C6H4N(CH3)2). 83,7 (s, =C(CN)2). 112,5 (s, CN). 113,75 (s, CN). 129,62 (s, CH=C(CN)2). 129,94 (2C, s, Ph). 130,5 (2C, s, Ph). 132,5 (s, Ph). 150,1 (s, Ph). FTIR (KBr) cm-1 :

2231 (CN),

1587 (C=C). MS (EI) m/z (%):

197 [M]+ (100). O NH2 CN NO2 Linear formula : C20H13N3O3 Molecular weight :

343 g/mol O NH2 CN O2 N Linear formula : C20H13N3O3 Molecular weight :

343 g/mol CN CN (CH3)2N Linear formula : C12H11N3 Molecular weight :

197 g/mol Supplementary Material (ESI) for Green Chemistry This journal is (c) The Royal Society of Chemistry