Molecules 2019, 24, 3819
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2‐(2‐((5H‐[1,2,4]triazino[5,6‐b]indol‐3‐yl)thio)‐1‐(4‐methoxyphenyl)
ethylidene)‐N‐(3,4‐
1
dichlorophenyl)hydrazine‐1‐carbothioamide (18) Yield: 71%; H‐NMR: (500 MHz, DMSO‐d6): δ 12.6 (s, 2H,
NH), 11.25 (s, 1H, NH), 8.28 (d, J = 6.45 Hz, 1H, Ar), 8.10 (d, J = 7.3 Hz, 2H, Ar), 7.69 (m, 2H, Ar), 7.61
(s, 1H, Ar), 7.55 (d, J = 6.7 Hz, 1H, Ar), 7.43 (t, J = 6.3 Hz, 2H, Ar), 7.12 (d, J = 7.35 Hz, 2H, Ar), 4.9 (s,
13
2H, CH2), 3.81(s, 3H, OCH3). C‐NMR (125 MHz, DMSO‐d6): δ 171.9, 165.8, 163.1, 159, 150.9, 141.2,
131.8, 131.8, 130.3, 128.2, 127, 126.9, 126.7, 123, 121.3, 121.2, 119.7, 119.7, 118.3 114.1, 114, 111, 104, 55.2,
+
38.2. HREI‐MS: m/z, calcd for C25H19Cl2N7OS2 [M] 567.0470; found: 567.0458.
2‐(2‐((5H‐[1,2,4]triazino[5,6‐b]indol‐3‐yl)thio)‐1‐([1,1′‐biphenyl]‐4‐yl)ethylidene)‐N‐(3,4‐
1
dichlorophenyl)hydrazine‐1‐carbothioamide (19) Yield: 77%; H‐NMR: (500 MHz, DMSO‐d6): δ 12.5 (s, 2H,
NH), 11.3 (s, 1H, NH), 8.27 (d, J = 6.5 Hz, 1H, Ar), 8.21 (d, J = 6.95 Hz, 2H, Ar), 7.91 (d, J = 6.9 Hz, 2H,
Ar), 7.80 (d, J = 6.2 Hz, 2H, Ar), 7.69 (d, J = 7Hz, 2H, Ar), 7.55 (m, 4H, Ar), 7.47(m, 3H, Ar), 5.03 (s, 2H,
13
CH2). C‐NMR (125 MHz, DMSO‐d6): δ 192.8, 166.2, 163.1, 146.4, 144.8, 141, 139.5, 139.4, 138.8, 134.7,
133, 129.0, 129.0, 128.9, 128.4, 127.5, 127.0, 126.9, 126.8, 126.4, 126.2,122.6, 122.3, 121.4, 119.8, 117.5,
+
112.6, 111.0, 106.9, 38.2. HREI‐MS: m/z, calcd for C30H21Cl2N7S2 [M] 613.0677; found: 613.0664.
2‐(2‐((5H‐[1,2,4]triazino[5,6‐b]indol‐3‐yl)thio)‐1‐(p‐tolyl)ethylidene)‐N‐(2,6‐dimethylphenyl)hydrazine‐1‐
1
carbothioamide (20) Yield: 68%; H‐NMR: (500 MHz, DMSO‐d6): δ 11.25 (s, 2H, NH), 10.86 (s, 1H, NH),
7.79 (d, J = 6.6 Hz, 2H, Ar), 7.53 (d, J = 4.1 Hz, 3H, Ar), 7.35 (t, J = 6.45 Hz, 1H, Ar), 7.23 (d, J = 6.5 Hz,
3H, Ar), 7.10 (t, J = 6.3 Hz, 1H, Ar), 6.97 (d, J = 6.5, 1H, Ar), 2.3(s, 6H, CH3), 4.8 (s, 2H, CH2), 1.91 (s,
13
3H, CH3). C‐NMR (125 MHz, DMSO‐d6): δ 171.9, 165.8, 163.1, 151.1, 141.2, 137.2, 131.9, 131.2, 130.4,
129.3, 129.3, 129.2, 129.2, 125.6, 125.6, 125.4, 122.3, 121.2, 119.7, 119.7, 111.0, 109.7, 105.8, 38.2, 21.0, 21.0,
+
20.7. HREI‐MS: m/z, calcd for C27H25N7S2 [M] 511.1613; found: 511.1600.
2‐(2‐((5H‐[1,2,4]triazino[5,6‐b]indol‐3‐yl)thio)‐1‐(p‐tolyl)ethylidene)‐N‐(3,4‐dichlorophenyl)hydrazine‐1‐
1
carbothioamide (21) Yield: 68%; H‐NMR: (500 MHz, DMSO‐d6): δ 11.25 (s, 2H, NH), 10.86 (s, 1H, NH),
7.77 (d, J = 6.4 Hz, 2H, Ar), 7.54 (d, J = 4.8 Hz, 2H, Ar), 7.32 (t, J = 6.2 Hz, 1H, Ar), 7.23 (d, J = 6.5 Hz,
13
3H, Ar), 7.10 (t, J = 6.25 Hz, 2H, Ar), 6.97 (s, 1H, Ar), 4.9 (s, 2H, CH2), 1.91 (s, 3H, CH3). C‐NMR (125
MHz, DMSO‐d6): δ 171.9, 165.8, 163.1, 159, 150.9, 141.2,131.8, 131.8, 130.3, 128.2, 127, 126.9, 126.7, 123,
121.3, 121.2, 119.7, 119.7, 118.3 114.1, 114, 111, 104, 38.2, 20.1. HREI‐MS: m/z, calcd for C25H19Cl2N7S2
+
[M] 551.0520; found: 551.0510.
2‐(2‐((5H‐[1,2,4]triazino[5,6‐b]indol‐3‐yl)thio)‐1‐(4‐methoxyphenyl)ethylidene)‐N‐(2,3‐
1
dimethylphenyl)hydrazine‐1‐carbothioamide (22) Yield: 62%; H‐NMR: (500 MHz, DMSO‐d6): δ 11.25 (s,
2H, NH), 10.86 (s, 1H, NH), 7.79 (d, J = 6.6 Hz, 2H, Ar), 7.51 (d, J = 4.5 Hz, 3H, Ar), 7.30 (t, J = 6.45 Hz,
1H, Ar), 7.20 (d, J = 6.7 Hz, 3H, Ar), 7.10 (t, J = 6.3 Hz, 1H, Ar), 6.93 (d, J = 6.5, 1H, Ar), 4.8 (s, 2H, CH2),
13
3.8 (s, 3H, OCH3), 2.3 (s, 6H, CH3). C‐NMR (125 MHz, DMSO‐d6): δ 171.9, 165.8, 163.1, 151.1, 141.2,
137.2, 131.9, 131.2, 130.4, 129.3, 129.3, 129.3, 129.2, 125.6, 125.6, 125.4, 122.3, 121.2, 119.7, 119.7, 111.0,
+
109.7, 105.8, 55.2, 38.2, 21.0, 21.0. HREI‐MS: m/z, calcd for C27H25N7OS2 [M] 527.1562; found: 527.1551.
2‐(2‐((5H‐[1,2,4]triazino[5,6‐b]indol‐3‐yl)thio)‐1‐(3‐nitrophenyl)ethylidene)‐N‐(2,3‐
1
dichlorophenyl)hydrazine‐1‐carbothioamide (23) Yield: 65%; H‐NMR (500 MHz, DMSO‐d6): δ 11.29 (s,
2H, NH), 10.86 (s, 1H, NH), 8.72 (d, J = 6.4 Hz, 1H, Ar), 8.37 (m, 1H, Ar), 8.23 (d, J = 6.2, 1H, Ar), 7.96
(s, 1H, Ar), 7.75 (m, 3H, Ar), 7.56 (d, J = 6.25, 1H, Ar), 7.37 (t, J = 6.25, 1H, Ar), 7.12 (t, J = 6.25, 1H, Ar),
13
6.98 (d, J = 6.5, 1H, Ar), 4.8 (s, 2H, CH2). C‐NMR (125 MHz, DMSO‐d6): δ 171.9, 165.8, 163.1, 159,
150.9, 141.2, 131.8, 131.8, 130.3, 129.2, 127, 126.9, 126.7, 123, 122.3, 121.2, 119.7, 119.7, 118.3 114.1, 114,
+
111, 104, 38.2. HREI‐MS: m/z, calcd for C24H16Cl2N8O2S2 [M] 582.0215; found: 582.0202.
2‐(2‐((5H‐[1,2,4]triazino[5,6‐b]indol‐3‐yl)thio)‐1‐([1,1′‐biphenyl]‐4‐yl)ethylidene)‐N‐phenylhydrazine‐1‐
1
carbothioamide (24) Yield: 74%; H‐NMR (500 MHz, DMSO‐d6): δ 11.27 (s, 2H, NH), 10.86 (s, 1H, NH),
8.2 (d, J = 6.8 Hz, 2H, Ar), 7.75 (m, 7H, Ar), 7.55 (d, J = 6.2 Hz, 1H, Ar), 7.49 (t, J = 6.3 Hz, 3H, Ar), 7.39
13
(m, 3H, Ar), 7.19 (t, J = 6.25 Hz, 1H, Ar), 6.98 (d, J = 6.45 Hz, 1H, Ar), 5.03 (s, 2H, CH2). C‐NMR (125