PDF《Supporting Information》

2010 S7 Characterisation of benzo[a]anthracenes: Purification of these products as follows: after

6 hrs reaction, the obtained residue was purified by silica gel flash chromatography (n-hexane/AcOEt: 80/20). 10-methyl-7-phenyl-8,9-dihydro-7H-12- oxa-9,11-diaza-benzo[a]anthracene-8-one(5a): Yellow solid, mp = 110-112°C.

1 H NMR (CDCl3,

300 MHz) δ en ppm : 2,51 (3H, s, CH3 ). 5,09 (1H, s, H-7). 7,25 (1H, d, JHH = 10,17 Hz, H-6). 7,24 - 7,37 (6H, m, H-2'

, 3'

, 4'

, 5'

, 6'

, NH). 7,52 -7,61 (3H, m, H-2, 3, 5). 7,79 (1H, d, JHH =

9 Hz, H-4). 8,12 (1H, d, JHH =

9 Hz, H-1).

13 C NMR (CDCl3,

75 MHz) δ en ppm : 25,56 (s, CH3). 43,89 (s, C-7). 93,43 (s, Cq). 115,59 (s, Cq). 115,6 (s, Cq). 120,98 (s, C-1). 123,36 (s, C-12b). 125,7 (s, C-5). 126,22 (s, C-6). 127,38 (s, C-2 ou C-3). 127,44 (s, C-2 ou C- 3). 127,91 (s, C-4). 128,39 (s, C-4'

). 128,56 (s, C-3'

, 5'

). 129,38 (s, C-2'

, 6'

). 133,64 (s, Cq). 141,98 (s, Cq). 143,95 (s, C-12a). 152,42 (C-11a). 170,63 (s, C-8). FTIR (KBr) cm-1 :

3265 (NH),

1720 (CO lactone). MS (EI) m/z :

340 (M+ ). 10-methyl-7-(4-methylphenyl)-8,9-dihydro-7H- 12-oxa-9,11-diaza-benzo[a]anthracene-8-one (5b) : Yellow solid, mp = 148-149°C.

1 H NMR (CDCl3,

300 MHz) δ en ppm : 2,31 (3H, s, C6H4CH3). 2,51 (3H, s, CH3 ). 5,05 (1H, s, H- 7). 7,02 (1H, d, JHH = 9,81 Hz, H-6). 7,2 -7,4 (5H, m, H-2'

, 3'

, 5'

, 6'

, NH). 7,5 -7,65 (3H, m, H-2, 3, 5). 7,78 (1H, d, JHH =

9 Hz, H-4). 8,11 (1H, d, JHH =

9 Hz, H-1).

13 C NMR (CDCl3,

75 MHz) δ en ppm : 21,23 (s, C6H4CH3). 25,55 (s, CH3). 43,49 (s, C-7). 93,91 (s, Cq). 115,22 (s, Cq). 115,77 (s, Cq). 120,96 (s, C-1). 123,36 (s, C-12b). 125,74 (s, C-5). 126,15 (s, C-6). 127,32 (s, C-2 ou C-3). 127,46 (s, C-2 ou C-3). 127,89 (s, C-4). 128,44 (s, C-3'

, 5'

). 130,06 (s, C-2'

, 6'

). 133,60 (s, Cq). 138,17 (s, Cq). 139,15 (s, Cq). 143,9 (s, C-12a). 152,21 (........