M. S. Khan et al. / Bioorg. Med. Chem. 22 (2014) 1195–1200
1199
4.3.6. 4-Bromo-N-(11H-indeno[1,2-b]quinoxalin-11-
ylidene)benzohydrazide (3f)
122.9 (C-40), 122.5 (C30 & C50). EI-MS (m/z %):384.0 (M+, 3.8),
385.0 (M++1, 1.6), 386.0 (M++2, 1.4), 356.0 (M+ꢀ28, 1), 245.2
(M+ꢀ139, 72.2), 217.2 (M+ꢀ167, 100), 190.2 (217-HCN, 14.8),
141.1 (M++2ꢀ245, 5.8), 139.1 (M+ꢀ245, 18.9). Anal. Calcd for
Yellow solid. Yield: 74%. Mp 245–248 °C. 1H NMR (CDCl3
600 MHz): dH: 14.29 (1H, s, NH), 8.19-8.23 (2H, m, H-9 & H-6),
8.12-8.14 (1H, m, H-20& H-60), 8.05-8.06 (3H, m, H30 & H50), 7.78-
C
22H13ClN4O (384.82): C, 68.67; H, 3.41; N, 14.56. Found: C,
7.87 (4H, m, H-7, H-8, H-1, H-4), 7.61 (2H, m, H-2 & H-3).13
C
68.78; H, 3.23; N, 14.61.
NMR (CDCl3 150 MHz): dC: 163.4 (C@O), 154.1 (C@N), 147.8
(C-4b), 143.3 (C-10a), 142.2 (C-5a), 139.8 (C-9a), 137.8 (C-10),
135.9 (C-30, C-50), 133.1 (C-4a), 132.4 (C-11a), 132.3 (C-3), 131.6
(C-8), 131.5 (C-7), 130.1 (C-1), 129.8 (C-9), 129.3 (C-6), 129.1 (C-2),
127.6 (C-40), 122.8 (C-4), 122.5 (C20& C60).EI-MS (m/z, %): 429.9
(M+, 3.5) 431.1 (M++1, 6.3), 432.0 (M++2, 5.6) 400.1 (M+ꢀ28, 0.8),
245.0 (M+ꢀ184.9, 88.8), 217.0 (M+ꢀ212.9, 100), 190.1 (217-HCN,
16.8) 184.9 (M++2ꢀ245, 10.5) 182.9 (M+ꢀ245, 11.2). Anal. Calcd
for C22H13BrN4O (429.27): C, 61.55; H, 3.05; N, 13.05. Found: C,
61.72; H, 3.14; N, 12.89.
4.3.10. N-(11H-Indeno[1,2-b]quinoxalin-11-ylidene)-3-
iodobenzohydrazide (3j)
Yellow solid. Yield: 80%. Mp 246–248 °C.IR (KBr): mmax cmꢀ1
:
3217.27 (NH, amide), 3120.00 (Ar-H), 1701.22 (C@O), 1589.34
(C@N), 629.44 (C-I).1H NMR (CDCl3 600 MHz): dH: 14.36 (1H, s,
NH), 8.55 (1H, s, H-20), 8.27 (1H, d, J = 7.5 Hz, H-60), 8.21–8.22 (3H,
m, H-9, H-6, H40), 8.16 (1H, d, J = 8.4 Hz, H-1), 8.00 (1H, d, J = 7.2 Hz,
H-4), 7.87 (1H, t, J = 7.2 Hz, H-8), 7.83 (1H, t, J = 7.2 Hz, H-7), 7.62
(2H, m, H-2 & H-3), 7.38 (1H, t, J = 7.5 Hz, H-50). 13C NMR (CDCl3
150 MHz): dC: 162.5 (C@O), 154.0 (C@N), 147.9 (C-4b), 143.5 (C-
10a), 142.1 (C-9a), 141.5 (C-40), 139.9 (C-5a), 137.8 (C-4a), 136.3
(C-20), 135.9 (C-10), 134.7 (C-11a), 132.4 (C-3), 131.7 (C-8), 131.6
(C-7), 130.8 (C-50), 130.2 (C-1), 129.8 (C-9), 129.5 (C-6), 127.6 (C-2),
122.9 (C-4), 122.6 (C-60), 94.5 (C-30). EI-MS (m/z): 476.3 (M+, 25.5),
477.3 (M++1, 13.6), 478.3 (M++2, 2.7), 448.2 (M+ꢀ28, 10.1), 245.1
(M+ꢀ231, 95.7), 231.0 (M+ꢀ245, 37.1), 217 (M+ꢀ259.3, 100), 190.1
(217-HCN, 51.9). Anal. Calcd for C22H13IN4O (476.27): C, 55.48; H,
2.75; N, 11.67. Found: C, 55.21; H, 3.01; N, 11.59.
4.3.7. 2-Chloro-N-(11H-indeno[1,2-b]quinoxalin-11-
ylidene)benzohydrazide (3g)
Yellow solid. Yield: 76%. Mp 180–183 °C. IR (KBr): m :
max, cmꢀ1
3415.93 (NH, amide), 1774.51 (C@O), 1681.93 (C@N), 715.59 (C-
Cl). 1H NMR (CDCl3 600 MHz): dH: 14.00 (1H, s, NH), 8.23–8.26
(3H, m, H-9, H-6, H-1), 7.75–8.01 (3H, m, H-7, H-8, H-4), 7.41–
7.64 (6H, m, H-30, H-40, H-50, H-60, H-2, H-3). 13C NMR (CDCl3
150 MHz): dC: 163.8 (C@O), 153.9 (C@N), 143.2 (C-4b), 141.2 (C-
10a), 140.6 (C-9a), 140.3 (C-5a), 138.3 (C-4a), 135.2 (C-40), 134.1
(C-10), 132.7 (C-20), 132.7 (C-3), 131.8 (C-8), 131.7 (C-7), 131.3
(C-1), 131.0 (C-11a), 130.7 (C-9), 130.1 (C-6), 129.6 (C-30), 129.4
(C-60), 127.4 (C-2), 123.0 (C-4), 121.8 (C-50). EI-MS (m/z %): 384.0
(M+, 6.3), 385.0 (M++1, 3.0), 386.0 (M++2, 2.5), 356.0 (M+ꢀ28,
1.2), 245.0 (M+ꢀ139, 97.3), 217.0 (M+ꢀ167, 100), 190.1 (217-
HCN, 20.3), 140.9 (M++2ꢀ245, 6.8), 138.9 (M+ꢀ245, 20.9). Anal.
Calcd for C22H13ClN4O (384.82): C, 68.67; H, 3.41; N, 14.56. Found:
C, 68.89; H, 3.47; N, 14.44.
4.3.11. N-(11H-Indeno[1,2-b]quinoxalin-11-ylidene)-4-
iodobenzohydrazide (3k)
Yellow solid. Yield: 70%. Mp 230–232 °C. IR (KBr): mmax cmꢀ1
:
3221.12 (NH, amide), 3047.43 (Ar-H), 1707.00 (C@O), 1585.49
(C@N), 765.74 (C-I). 1H NMR (CDCl3 600 MHz): dH: 14.33 (1H, s,
NH), 8.29–8.13 (3H, m, H-9, H-6, H-1), 7.91-8.10 (5H, m, H-3 , H-
50, H-20, H-60, H-4), 7.80–7.90 (2H, m, H-8, H-7), 7.59-7.69 (2H,
m, H-2, H-3). EI-MS (m/z): 476.4 (M+, 6.1), 477.3 (M++1), 448.3
(M+ꢀ28, 2.4), 245.2 (M+ꢀ231, 91.4), 231.1 (M+ꢀ245, 17.2), 217.2
(M+ꢀ259.3, 100), 190.2 (217-HCN, 12.1). Anal. Calcd for C22H13IN4O
(476.27): C, 55.48; H, 2.75; N, 11.67. Found: C, 55.67; H, 2.98; N,
11.43.
4.3.8. 3-Chloro-N-(11H-indeno[1,2-b]quinoxalin-11-
ylidene)benzohydrazide (3h)
Yellow solid. Yield: 72%. Mp 240–242 °C.IR (KBr): mmax cmꢀ1
:
3236.55 (NH, amide), 3074.53 (Ar-H), 1718.58 (C@O), 1566.20
(C@N), 759.95 (C-Cl). 1H NMR (CDCl3 600 MHz): dH: 14.38 (1H, s,
NH), 8.21–8.22 (3H, m, H-9, H-6, H-20), 8.15–8.17 (2H, m, H-60,
H-1), 8.11 (1H, d, J = 7.2 Hz, H-40), 7.87 (1H, dt, J = 7.5 Hz, 1.2 Hz,
H-8), 7.83 (1H, dt, J = 7.5 Hz, 1.2 Hz, H-7), 7.57–7.66 (4H, m, H-50,
H-4, H-2 & H-3).13C NMR (CDCl3 150 MHz): dC: 162.7 (C@O),
154.1 (C@N), 147.9 (C-4b), 143.5 (C-10a), 142.2 (C-5a), 139.9 (C-
9a), 137.8 (C-4a), 135.9 (C-10), 135.1 (C-30), 134.5 (C-11a), 132.7
(C-40), 132.4 (C-3), 131.7 (C-8), 131.6 (C-7), 130.4 (C-50), 130.2
(C-1), 129.8 (C-9), 129.2 (C-6), 127.8 (C-2), 126.3 (C-4), 122.9 (C-
20), 122.6 (C-60). EI-MS (m/z):384.0 (M+, 3.3), 385.1 (M++1, 1.3),
386.0 (M++2, 1.3), 245.2 (M+ꢀ139, 57.5), 217.2 (M+ꢀ167, 100),
190.3 (217-HCN, 13.6), 141.2 (M++2ꢀ245, 2.7), 139.2 (M+ꢀ245,
8.4). Anal. Calcd for C22H13ClN4O (384.82): C, 68.67; H, 3.41; N,
14.56. Found: C, 68.73; H, 3.26; N, 14.81.
4.3.12. N-(11H-Indeno[1,2-b]quinoxalin-11-ylidene)-4-
methylbenzohydrazide (3l)
Yellow solid. Yield: 69%. Mp 198–200 °C. IR (KBr): mmax cmꢀ1
:
3224.98 (NH, amide), 3043.67 (Ar-H), 1699.29 (C@O), 1608.63
(C@N). 1H NMR (CDCl3 600 MHz): dH: 14.27 (1H, s, NH), 8.09–
8.22 (6H, m, H-9, H-6, H-20, H-60, H-1 & H-4), 7.86 (1H, t,
J = 7.5 Hz, H-8), 7.80 (1H, t, J = 7.5 Hz, H-7), 7.61 (2H, m, H-2 & H-
3), 7.44 (2H, d, J = 7.2 Hz, H-30 & H-50), 2.51 (3H, s, H-CH3). 13C
NMR (CDCl3 150 MHz): dC: 164.2 (C@O), 154.0 (C@N), 148.1 (C-
4b), 143.4 (C-10a), 142.6 (C-9a), 141.9 (C-5a), 140.0 (C-40), 138.2
(C-4a), 135.7 (C-30 & C-50), 132.4 (C-3), 131.5 (C-20 & C-60), 131.4
(C-10), 130.0 (C-8 & C-7), 129.8 (C-9), 129.7 (C-6), d129.2 (C-11a),
127.9 (C-1), 122.8 (C-2), 122.5 (C-4), 21.7 (C-CH3). EI-MS (m/z,
%): 364.3 (M+, 11.6), 336.2 (Mꢀ28, 7), 245.2 (Mꢀ119.1, 83), 217.2
(Mꢀ147, 100), 190.1 (217-HCN, 9), 119.1 (Mꢀ245.2, 46.6). Anal.
Calcd for C23H16N4O (364.40): C, 75.81; H, 4.43; N, 15.38. Found:
C, 76.01; H, 4.29; N, 15.52.
4.3.9. 4-Chloro-N-(11H-indeno[1,2-b]quinoxalin-11-
ylidene)benzohydrazide (3i)
Yellow solid. Yield: 78%. Mp: 234–238 °C.IR (KBr): mmax cmꢀ1
:
3199.91 (NH, amide), 3059.10 (Ar-H), 1703.14 (C@O), 1637.56
(C@N), 756.10 (C-Cl). 1H NMR (CDCl3 600 MHz): dH: 14.30 (1H, s,
NH), 8.20 (2H, m, H-9 & H-6), 8.14 (3H, m, H-20, H-60, H-1), 8.05
(1H, d, J=7.2 Hz, H-4), 7.87 (1H, t, J = 7.2 Hz, H-8), 7.82 (1H, t,
J = 7.2 Hz, H-7), 7.62 (4H, m, H-30, H-50, H-2, H-3).13C NMR (CDCl3
150 MHz): dC: 163.3 (C@O), 154.2 (C@N), 147.9 (C-4b), 143.2 (C-
10a), 142.2 (C-9a), 139.9 (C-5a), 139.1 (C-4a), 137.9 (C-10), 135.9
(C-40), 132.4 (C-3), 131.7 (C-8), 131.6 (C-7), 131.2 (C-11a), 130.1
(C-20 & C-60), 129.9 (C-1), 129.3 (C-9), 129.2 (C-6) 129.1 (C-2),
4.3.13. 2-Amino-N-(11H-indeno[1,2-b]quinoxalin-11-
ylidene)benzohydrazide (3m)
Red solid. Yield: 85%. Mp 228–230 °C. IR (KBr): mmax cmꢀ1
:
3560.59 (NH, amide), 3417.86 & 3309.85 (NH2), 3055.24 (Ar-H),
1680.00 (C@O), 1554.63 (C@N), 1242.16 (C-N).1H NMR (CDCl3
600 MHz): dH: 14.29 (1H, s, NH),8.13–8.26 (4H, m, H-9, H-6, H-1,
H-60), 7.92–7.97 (2H, m, H-7 & H-8), 7.75–7.86 (3H, m, H-4, H-3,
H-2), 7.61-7.63 (3H, m, H-40, H-50, H-30). EI-MS (m/z %): 365.1
(M+, 57.1), 337.0 (M+ꢀ28, 1.6), 245.0 (M+ꢀ120, 83.2), 217.0