GANTA et al., Orient. J. Chem., Vol. 32(5), 2673-2683 (2016)
2680
MHz, DMSO-d6): d 149.96, 139.33, 135.03, 132.85,
128.77, 127.93, 127.23, 126.93, 125.51, 124.84,
124.33, 123.42, 120.94, 117.93, 117.36, 112.32,
29.70. HRMS (ESI) m/z:calc. for [M+H+] C32H22F2N4:
500.54; found: 500.98
7.84(d, J= 7.74 Hz, 2H), 8.19(s,1H), 10.69(s, 2H).13C
NMR (75 MHz, DMSO-d6): d 152.61, 150.04, 139.44,
133.25, 131.70, 129.33, 128.36, 127.85, 127.68,
126.50, 125.80, 125.50, 124.19, 117.91, 117.55,
112.04, 110.50, 100.66, 55.06, 30.56, 29.50.HRMS
(ESI) m/z:calc.for [M+H+] C34H24N4O2:524.22;found:
524.91.
3c) 3, 3'-((1, 3-diphenyl-1H-pyrazol-4-yl)
methylene) bis (5-chloro-1H-indole)
1
Pale red Solid. M.P: 202-2040C H NMR
3g) 3, 3'-((1-phenyl, 3-3, 4, 5 tri methoxy phenyl-
1H-pyrazol-4-yl) methylene) bis (1H-indole)
White Solid. M.P: 233-2360C 1H NMR (300
(300 MHz, DMSO-d6): d 5.84(s, 1H), 6.82(d, J=
1.88 Hz, 2H), 7.11-7.32(m, 8H), 7.36- 7.44(m,
5H), 7.65-7.71(m, 4H), 10.12(s, 2H). 13C NMR (75
MHz, DMSO-d6): d 150.01, 139.33, 135.25, 132.80,
128.71, 127.91, 127.62, 127.24, 125.48, 124.61,
124.22, 123.57, 121.02, 117.98, 117.39, 112.67,
111. 27, 29.66.HRMS (ESI) m/z: calc. for [M+H+]
C32H22Cl2N4: 532.12; found: 532.74
MHz, DMSO-d6): d 2.57-2.96(m, 6H), 3.72(s, 3H),
5.92(s, 1H), 6.89-6.93(m, 6H), 7.06(t, J= 7.36 &
15.10 Hz, 2H), 7.21(t, J= 7.17 & 14.54 Hz, 1H), 7.32-
7.42(m, 6H), 7.66-7.91 (m,3H), 10.52 (brs, 2H).13C
NMR (75 MHz, DMSO-d6): d 152.59, 149.51, 139.39,
137.01, 136.70, 129.15, 128.58, 127.73, 126.08,
125.62, 125.00, 123.65, 120.86, 118.60, 118.15,
117.88, 111.36, 104.56, 59.83, 54.92, 30.06.HRMS
(ESI) m/z:calc.for [M+H+] C35H30N4O3:555.64;found:
555.09
3d) 3, 3'-((1, 3-diphenyl-1H-pyrazol-4-yl)
methylene) bis (5-bromo-1H-indole)
1
Pale pink Solid. M.P: 256-2580C. H NMR
(300 MHz, DMSO-d6): d 5.81(s, 1H), 6.80-6.90 (m,
6H), 7.22-7.42(m, 7H), 7.51(s, 1H), 7.63-7.72(m,
5H), 10.12(s, 2H). 13C NMR (75 MHz, DMSO-d6):
d 158.04, 154.95, 150.06, 139.36, 133.09, 132.83,
128.66, 127.82, 127.24, 127.12, 126.21, 126.08,
125.38, 124.98, 124.31, 117.91, 111.63, 111.50,
109.16, 108.83, 103.56, 103.26, 29.89.HRMS
(ESI) m/z:calc.for [M+H+] C32H22Br2N4:620.12;found:
620.99
3h) 3, 3'-((1-phenyl, 3-3, 4, 5 tri methoxy phenyl-
1H-pyrazol-4-yl) methylene) bis (5-fluoro-
indole)
1
Pale pink Solid. M.P: 284-2860C H NMR
(300 MHz, DMSO-d6): d 3.41(s, 6H), 3.79(s, 3H),
5.84(s, 1H), 6.87-6.92(m, 4H), 7.06 (dd, J= 2.07 &
8.68 Hz, 2H), 7.20-7.44(m, 7H), 7.54(s, 1H), 7.66(d,
J= 7.74 Hz, 2H), 10.14(s, 2H). 13C NMR (75 MHz,
DMSO-d6): d 152.42, 149.58, 139.25, 136.87,
135.03, 128.75, 128.30, 127.28, 126.85, 125.48,
125.05, 124.07, 123.49, 121.02, 117.90, 117.68,
117.33, 112.34, 104.24, 60.01, 56.63, 54.81, 29.82.
HRMS (ESI) m/z: calc. for [M+H+] C35H28F2N4O3:
591.92; found: 591.06
3e) 3, 3'-((1, 3-diphenyl-1H-pyrazol-4-yl)
methylene) bis (5-iodo-1H-indole)
White Solid. M.P: 206-2080C 1H NMR (300
MHz, DMSO-d6): d 5.84(s, 1H), 6.82(d, J= 1.88 Hz,
2H), 7.17-7.44(m, 12H), 7.57(s, 1H), 7.65-7.71(m,
4H), 10.08(s, 2H). 13C NMR (75 MHz, DMSO-d6):
d 158.87, 155.78, 150.89, 140.18, 133.92, 133.66,
129.49, 128.66, 128.07, 127.95, 127.04, 126.91,
126.21, 125.81, 125.14, 118.74, 112.46, 112.33,
109.99, 109.66, 104.49, 104.09, 30.72.HRMS
(ESI) m/z:calc. for [M+H+] C32H22I2N4:716.64;found:
716.99
3i) 3, 3'-((1-phenyl, 3-3, 4, 5 tri methoxy phenyl-1H-
pyrazol-4-yl) methylene) bis (5-chloro-indole)
1
White Solid. M.P: 212-2150C H NMR
(300 MHz, DMSO-d6): d 3.41(s, 6H), 3.79(s, 3H),
5.83(s, 1H), 6.86-6.91(m, 4H), 7.16-7.25(m, 3H),
7.30(d, J=8.8Hz, 2H), 7.37-7.46(m, 4H), 7.54(s,
1H), 7.67(d, J= 7.74Hz, 2H), 10.43(s,2H).13C NMR
(75 MHz, DMSO-d6): d 152.46, 149.50, 136.94,
135.33, 128.85, 128.33, 127.58, 127.31, 125.54,
125.00, 124.16, 123.52, 120.67, 117.89, 117.21,
113.01, 111.13, 104.32, 59.95, 54.86, 29.76.HRMS
(ESI) m/z: calc. for [M+H+] C35H28Cl2N4O3: 623.53;
found: 623.03
3f)3,3'-((1,3-diphenyl-1H-pyrazol-4-yl)methylene)
bis (5-methoxy-1H-indole)
Pale pink Solid. M.P: 198-2000C 1H NMR
(300 MHz, DMSO-d6): d 3.55(s, 6H), 5.80 (s, 1H),
6.65-6.71(m, 4H), 6.99 (d, J= 2.07 Hz, 2H), 7.22-7.28
(m, 3H), 7.33- 7.47(m, 5H), 7.68(d, J= 6.42 Hz, 2H),