M. Ghashang et al.
11-Amino-12-(3-methylphenyl)-7,8,9,10,12,13-hexahydro-5-oxa-6,13-diaza-
indeno[1,2-b]anthracene (6i)
1
IR (KBr, cm-1): 3,417, 3,372, 2,930, 1,676, 1,630, 1,472, 1,237, 1,170; H NMR
(500 MHz, DMSO-d6) d: 1.77 (m, 4H, CH2), 2.07 (m, 2H, CH2), 2.28 (s, 3H, CH3),
2.37 (m, 2H, CH2), 5.30 (s, 1H, CH), 5.61 (s, 2H, NH2), 6.90–7.03 (m, 2H, Ar–H);
7.15–7.29 (m, 4H, Ar–H); 7.49 (d, 1H, J = 7.2, Ar–H); 7.69 (d, 1H, J = 7.8, Ar–
H), 9.89 (bs, 1H, NH) ppm; 13C NMR (125 MHz, DMSO-d6) d: 19.0, 22.5, 27.7,
31.5, 32.5, 35.2, 103.9, 105.5, 110.8, 117.3, 121.4, 123.0, 128.4, 128.9, 130.6,
131.2, 135.5, 135.8, 137.8, 157.9, 161.0, 165.8 ppm; MS (ESI): m/z 382 (M ? H)?;
Anal. Calcd for C25H23N3O: C, 78.71; H, 6.08; N, 11.02 %. Found: C, 78.63; H,
6.07; N, 11.00 %.
11-Amino-12-(2-chlorophenyl)-7,8,9,10,12,13-hexahydro-5-oxa-6,13-diaza-
indeno[1,2-b]anthracene (6j)
1
IR (KBr, cm-1): 3,421, 3,364, 2,932, 1,674, 1,632, 1,470, 1,233, 1,171; H NMR
(500 MHz, DMSO-d6) d: 1.80 (m, 4H, CH2), 2.11 (m, 2H, CH2), 2.40 (m, 2H, CH2),
5.27 (s, 1H, CH), 5.64 (s, 2H, NH2), 6.92–7.06 (m, 2H, Ar–H); 7.12–7.30 (m, 4H,
Ar–H); 7.48 (d, 1H, J = 7.4, Ar–H); 7.71 (d, 1H, J = 7.8, Ar–H), 9.87 (bs, 1H, NH)
ppm; 13C NMR (125 MHz, DMSO-d6) d: 22.4, 27.5, 31.6, 32.7, 35.0, 103.7, 105.9,
110.9, 116.7, 121.0, 122.5, 127.7, 128.4, 130.3, 131.3, 135.6, 135.9, 137.4, 158.0,
160.5, 166.4 ppm; MS (ESI): m/z 402 (M ? H)?;Anal. Calcd for C24H20ClN3O: C,
71.73; H, 5.02; N, 10.46 %. Found: C, 71.64; H, 5.03; N, 10.44 %.
11-Amino-12-(3-bromophenyl)-7,8,9,10,12,13-hexahydro-5-oxa-6,13-diaza-
indeno[1,2-b]anthracene (6k)
1
IR (KBr, cm-1): 3,424, 3,360, 2,937, 1,672, 1,627, 1,464, 1,237, 1,173; H NMR
(500 MHz, DMSO-d6) d: 1.85 (m, 4H, CH2), 2.17 (m, 2H, CH2), 2.47 (m, 2H, CH2),
5.26 (s, 1H, CH), 5.60 (s, 2H, NH2), 6.88–7.00 (m, 2H, Ar–H); 7.16–7.33 (m, 4H,
Ar–H); 7.47 (d, 1H, J = 7.4, Ar–H); 7.73 (d, 1H, J = 8.0, Ar–H), 9.91 (bs, 1H, NH)
ppm; 13C NMR (125 MHz, DMSO-d6) d: 22.3, 27.6, 31.3, 32.5, 35.2, 103.5, 104.9,
111.4, 116.9, 120.8, 122.7, 128.4, 128.8, 130.4, 130.9, 134.7, 135.5, 137.3, 158.5,
160.7, 166.9 ppm; MS (ESI): m/z 447 (M ? H)?; Anal. Calcd for C24H20BrN3O: C,
64.58; H, 4.52; N, 9.41 %. Found: C, 64.54; H, 4.53; N, 9.35 %.
11-Amino-12-(4-fluorophenyl)-7,8,9,10,12,13-hexahydro-5-oxa-6,13-diaza-
indeno[1,2-b]anthracene (6l)
1
IR (KBr, cm-1): 3,411, 3,362, 2,940, 1,673, 1,625, 1,463, 1,235, 1,175; H NMR
(500 MHz, DMSO-d6) d: 1.81 (m, 4H, CH2), 2.15 (m, 2H, CH2), 2.45 (m, 2H, CH2),
5.28 (s, 1H, CH), 5.63 (s, 2H, NH2), 6.87–7.03 (m, 2H, Ar–H); 7.17–7.31 (m, 4H,
Ar–H); 7.52 (d, 1H, J = 7.2, Ar–H); 7.75 (d, 1H, J = 8.0, Ar–H), 9.89 (bs, 1H, NH)
ppm; 13C NMR (125 MHz, DMSO-d6) d: 22.2, 27.9, 30.7, 32.4, 34.7, 103.8, 104.8,
111.6, 117.4, 120.9, 122.8, 128.2, 128.6, 130.5, 131.1, 135.3, 135.7 137.7, 158.2,
123