MIRMIRAN-YAZDI et al./Turk J Chem
8.1 Hz, Ar-H), 8.73 (d, 1H, J = 7.8 Hz, Ar-H), 9.29–9.32 (m, 1H, Ar-H) ppm; 13 C NMR (75 MHz, CDCl3): δ
38.5 (CH), 55.4 (OCH3), 117.1, 117.8, 120.6, 121.3, 121.4, 122.4, 122.5, 124.7, 125.8, 126.4, 128.6, 128.8, 129.3,
129.6 (2x), 129.8, 130.4, 130.5 (2x), 130.6, 130.9, 132.2 (2x), 132.4, 138.3, 140.5, 141.7, 141.8, 146.4, 150.3,
155.7, and 157.2 (Colefinic and Carom) ppm; MS (m/z, %): 490 (M+ , 2); Anal. Calcd. for C34 H22 N2 O2 : C,
83.25; H, 4.52; N, 5.71 %. Found: C, 83.63; H, 5.01; N, 6.98 %.
3.2.6. 18-(4-Chlorophenyl)-18H -benzo[a]benzo[5,6]chromeno[2,3-c]phenazine (7a)
Yellow powder; yield 0.440 g (89%), mp 292–294 ◦ C; IR (KBr): νmax = 2920, 1651, 1625, 1593, 1528, 1345,
1286, 1177, 1043, 760 cm−1 1 H NMR (300 MHz, CDCl3): δ 6.02 (s, 1H, CH), 7.21 (d, 2H, J = 7.8 Hz, Ar-H),
;
7.46 (d, 2H, J = 7.8 Hz, Ar-H), 7.62–8.65 (m, 1H, Ar-H), 7.96–8.07 (m, 6H, Ar-H), 8.12–8.17 (m, 2H, Ar-H),
8.27–8.31 (m, 2H, Ar-H), 8.48 (d, 1H, J = 7.8 Hz, Ar-H), 8.62 (d, 1H, J = 7.8 Hz, Ar-H), 9.31 (d, 1H, J =
7.8 Hz, Ar-H) ppm; 13 C NMR (75 MHz, CDCl3): δ 39.2 (CH), 115.4, 116.1, 121.5, 121.8, 122.2, 123.1, 124.5,
125.6 (2x), 125.9, 127.2, 128.3, 128.7, 129.2, 129.4, 129.5, 129.7 (2x), 130.4, 130.9, 131.2 (2x), 131.5, 133.2 (2x),
141.5, 141.6, 142.5, 144.3, 144.9, 150.7, and 155.2 (Colefinic and Carom) ppm; MS (m/z, %): 494 (M+ , 12);
Anal. Calcd. for C33 H19 ClN2 O: C, 80.08; H, 3.87; N, 5.66 %. Found: C, 80.38; H, 3.98; N, 5.98 %.
3.2.7. 18-(4-Nitrophenyl)-18H -benzo[a]benzo[5,6]chromeno[2,3-c]phenazine (7b)
Yellow powder; yield 0.444 g (88%), mp 267–269 ◦ C; IR (KBr): νmax = 3012, 1657, 1635, 1592, 1536, 1342,
1265, 1187, 1071, 757 cm−1
;
1 H NMR (300 MHz, CDCl3): δ 5.94 (s, 1H, CH), 7.47–7.51 (m, 1H, Ar-H),
7.71–7.75 (m, 2H, Ar-H), 7.87–7.98 (m, 7H, Ar-H), 8.13 (d, 2H, J = 8.1 Hz, Ar-H), 8.20–8.23 (m, 1H, Ar-H),
8.30–8.37 (m, 3H, Ar-H), 8.61 (d, 1H, J = 8.1 Hz, Ar-H), 9.23–9.26 (m, 1H, Ar-H) ppm; 13 C NMR (75 MHz,
CDCl3): δ 40.7 (CH), 114.2, 117.5, 119.5, 121.2 (2x), 121.4, 122.7 (2x), 124.2, 125.8, 126.4, 128.3, 128.5, 128.7,
129.0 (2x), 129.5, 129.6, 130.7 (2x), 130.8, 130.9, 131.5, 132.0, 133.1, 140.4, 142.3, 142.5, 146.1, 146.4, 152.6,
and 156.1 (Colefinic and Carom) ppm; MS (m/z, %): 505 (M+ , 2); Anal. Calcd. for C33 H19 N3 O3 : C, 78.40;
H, 3.79; N, 8.31 %. Found: C, 78.18; H, 3.96; N, 8.02 %.
3.2.8. 18-(3-Nitrophenyl)-18H -benzo[a]benzo[5,6]chromeno[2,3-c]phenazine (7c)
Yellow powder; yield 0.429 g (85%), mp 248–250 ◦ C; IR (KBr): νmax = 3012, 1657, 1635, 1592, 1536, 1342,
1265, 1187, 1071, 757 cm−1 1 H NMR (300 MHz, CDCl3): δ 6.14 (s, 1H, CH), 7.35 (t, 1H, J = 7.8 Hz, Ar-H),
;
7.61 (t, 1H, J = 7.8 Hz, Ar-H), 7.86–8.14 (m, 10H, Ar-H), 8.31–8.35 (m, 2H, Ar-H), 8.47 (s, 1H, Ar-H), 8.62 (d,
1H, J = 8.1 Hz, Ar-H), 8.83 (d, 1H, J = 8.1 Hz, Ar-H), 9.17 (d, 1H, J = 8.1 Hz, Ar-H) ppm; 13 C NMR (75
MHz, CDCl3): δ 38.9 (CH), 116.4, 118.3, 119.7, 120.3, 121.6 (2x), 122.8, 123.9, 125.5, 125.7 (2x), 128.2, 128.7,
129.0 (2x), 129.2, 129.5, 129.7 (2x), 129.9, 130.4, 130.8, 130.9, 131.7, 132.2, 140.6, 141.2, 143.5, 145.4, 146.4,
150.8, and 157.3 (Colefinic and Carom) ppm; MS (m/z, %): 505 (M+ , 9); Anal. Calcd. for C33 H19 N3 O3 : C,
78.40; H, 3.79; N, 8.31 %. Found: C, 78.81; H, 4.05; N, 8.62 %.
3.2.9. 18-Phenyl-18H -benzo[a]benzo[5,6]chromeno[2,3-c]phenazine (7d)
Yellow powder; yield 0.382 g (83%), mp 277–278 ◦ C; IR (KBr): νmax = 3043, 1655, 1631, 1592, 1536, 1392,
1271, 1185, 1035, 757 cm−1
;
1 H NMR (300 MHz, CDCl3): δ 5.81 (s, 1H, CH), 7.09 (d, 1H, J = 7.8 Hz,
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