PDF《Supporting Information》

13 C), Mass Spectra and FTIR spectra are provided at the end of this document) All synthesized products were characterized by spectroscopic methods including

1 H NMR,

13 C, IR and EI mass spectrometry, as well as by their melting points. 2-1. Characterization of 2-amino-2-chromenes

4 2-Amino-3-cyano-4-phenyl-4H-benzo[h]chromene (4a): Yellow solid, mp = 207-210°C.

1 H NMR (CDCl3,

300 MHz) δ en ppm : 4,79 (2H, s, NH2). 4,86 (1H, s, H-4). 7,02 (1H, d, JHH = 8,4 Hz, H-5). 7,12 -7,38 (5H, m, H-2'

, 3'

, 4'

, 5'

, 6'

). 7,44 -7,6 (3H, m, H-6, 8, 9). 7,8 (1H, d, JHH = 7,8 Hz, H-7). 8,17 (1H, d, JHH = 7,8 Hz, H-10).

13 C NMR (CDCl3,

75 MHz) δ en ppm : 41,47 (s, C-4). 61,34 (s, C-3). 117,26 (s, CN). 119,75 (s, C-4a). 120,77 (s, C-10). 123,23 (s, C-10a). 124,62 (s, C-6), 126,22 (s, C-5). 126,66 (s, C-8). 126,74 (s, C-9). 127,36 (s, C-4'

). 127,74 (s, C-7). 128,84 (s, C-3'

, 5'

). 129,19 (s, C-2'

, 6'

), 133,3 (C-6a). 142,4 (C-1'

). 144,41(C-10b). 159,02 (C-2). FTIR (KBr) cm-1 :

3436 (CH),

3317 (NH2),

2183 (CN),

1655 (NH2). MS (EI) m/z (%) :

298 (M+ ), 221,(100). O NH2 CN Linear formula : C20H14N2O Molecular weight :

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

2010 S5 2-Amino-3-cyano-4-(4-methylphenyl)-4H- benzo[h]chromene (4b) : Yellow solid, mp = 206- 209°C.

1 H NMR ( CDCl3 ,

300 MHz ) δ en ppm : 2,35 (3H, s, C6H4CH3). 4,79 (2H, s, NH2 ). 4,84 (1H, s, H-4). 7,04 (1H, d, JHH = 8,4 Hz, H-5). 7,11- 7,37 (4H, m, H-2'

, 3'

, 5'

, 6'

). 7,45 -7,61 (3H, m, H-6, 8, 9). 7,8 (1H, d, JHH = 8,4 Hz, H-7). 8,20 (1H, d, JHH = 8,1 Hz, H-10).

13 C NMR (CDCl3,

75 MHz) δ en ppm : 21,38 (s, C6H4CH3), 41,37 (s, C- 4). 61,3 (s, C-3). 117,76 (s, CN). 119,75 (s, C-4a). 120,77 (s, C-10). 123,23 (s, C-10a). 124,90 (s, C- 6), 126,57 (s, C-5). 126,95 (s, C-8). 127,01 (s, C-9). 128,06 (s, C-7). 128,3 (s, C-3'

, 5'

). 128,92 (s, C-2'

, 6'

). 130,23 (s, C-6a). 133,59 (C-1'

). 137,32 (C-4'

). 141,86(C-10b). 159,28 (C-2). FTIR (KBr) cm-1 :

3435 (CH),

3320 (NH2),

2180 (CN),

1657 (NH2). MS (EI) m/z (%) :

312 (M+ ),

221 (100). 2-Amino-3-cyano-4-(4-methoxylphenyl)-4H- benzo[h]chromene (4c) : Yellow solid, mp = 182- 184°C.

1 H NMR (CDCl3,

300 MHz) δ en ppm : 3,5 (3H, s, C6H4OCH3). 4,81 (2H, s, NH2). 4,88 (1H, s, H-4). 7,03 (1H, d, JHH = 8,4 Hz, H-5). 7,23 -7,35 (4H, m, H-2'

, 3'

, 5'

, 6'

). 7,5 -7,59 (3H, m, H-6, 8, 9). 7,8 (1H, d, JHH = 8,1 Hz, H-7). 8,19 (1H, d, JHH = 7,8 Hz, H-10).

13 C NMR (CDCl3,

75 MHz) δ en ppm : 41,79 (s, C-4). 55,3 (s, C6H4OCH3). 61,65 (s, C-3). 117,58 (s, CN).

120 (s, C-4a). 121,1 (s, C-10). 123,55 (s, C-10a). 124,95 (s, C-6), 126,55 (s, C-5). 126,99 (s, C-8). 127,07 (s, C-9). 127,69 (s, C-7). 128,43 (s, C-3'

, 5'

). 128,17 (s, C-2'

, 6'

). 129,52 (s, C-1'

). 133,62 (C-6a). 144,74 (C-10b).

154 (s, C-4'

). 159,35 (C-2). FTIR (KBr) cm-1 :

3416 (CH),

3316 (NH2),

2183 (CN),

1633 (NH2). MS (EI) m/z (%) :

328 (M+ );

221 (100). 2-Amino-3-cyano-4-(4-chlorphenyl)-4H- benzo[h]chromene (4d) : Yellow solid, mp = 232-234°C.

1 H NMR (CDCl3,

300 MHz) δ en ppm : 4,81 (2H, s, NH2). 4,87 (1H, s, H-4). 6,99 (1H, d, JHH = 8,52 Hz, H-5).7,18 (2H, d, JHH = 8,4 Hz, H-2'

, 6'

). 7,31 (2H, d, JHH = 8,4 Hz, 3'

, 5'

). 7,52-7,62 (3H, m, H-6, 8, 9). 7,81 (1H, d, JHH = 7,35 Hz, H-7). 8,19 (1H, d, JHH = 7,92 Hz, H-10).