Molecules 2015, 20
16062
2,5-Bis[(4-benzylideneamino)-2,4-dihydro-1,2,4-triazol-3-thione-5-yl)propylthio]-1,3,4-thiadiazole (21).
This compound was obtained as white solid, Yield 91%; m.p. 186–188 °C. IR (υ, cm−1): 1624 (C=N),
1
1268 (C=S), 3084 (Ar-H), 3288–3329 (NH). H-NMR: δ 2.06–2.15 (m, 2H, CH2CH2CH2), 2.67–2.73
(m, 2H, CH2C=N), 2.80–2.88 (m, 2H, SCH2), 7.40–7.53 (m, 3H, Ar-H), 7.69–7.79 (m, 2H, Ar-H), 9.18
(s, 1H, H-C=N), 13.52 (s, 1H, NH triazole) ppm. 13C-NMR: δ 23.36 (CH2CH2CH2), 25.60 (CH2C=N),
32.83 (SCH2), 126.45, 128.79, 129.40, 134.80 (Ar-C), 162.08, 163.77, 165.94 (C=N), 173.41 (C=S)
ppm. ESI MS (m/z): 638.35 (M + H)+. Anal. Calcd for C26H26N10S5: C 48.88; H 4.10; N 21.92. Found:
C 48.98; H 4.26; N 21.77.
2,5-Bis[(4-(2-bromobenzylideneamino)-2,4-dihydro-1,2,4-triazol-3-thione-5-yl)-propylthio]-1,3,4-thiadiazole
(22). This compound was obtained as white solid, Yield 92% yield; m.p. 206–208 °C. IR (υ, cm−1): 1639
1
(C=N), 1247 (C=S), 3069 (Ar-H), 3214–3344 (NH). H-NMR: δ 2.02–2.11 (m, 2H, CH2CH2CH2),
2.63–2.71 (m, 2H, CH2C=N), 2.77–2.85 (m, 2H, SCH2), 7.45–7.58 (m, 2H, Ar-H), 7.73–7.82 (m, 2H,
Ar-H), 9.24 (s, 1H, H-C=N), 13.47 (s, 1H, NH triazole) ppm. 13C-NMR: δ 23.68 (CH2CH2CH2), 25.05
(CH2C=N), 32.64 (SCH2), 124.61, 127.80, 128.34, 131.87, 133.13, 141.80 (Ar-C), 162.34, 164.18,
165.86 (C=N), 173.89 (C=S) ppm. ESI MS (m/z): 793.69 (M + H)+. Anal. Calcd for C26H24Br2N10S5: C
39.20; H 3.04; N 17.58. Found: C 39.41; H 2.86; N 17.45.
4,4′-(1,3,4-Thiadiazol-2,5-diyl)bis-(sulfanediyl)bis-(N′-(4-benzylidene)butanehyd-razide) (23). This
compound was obtained as colorless crystals, Yield 93% yield; m.p. 136–138 °C. IR (υ, cm−1): 1669
1
(C=N), 1714 (C=O), 3064 (Ar-H), 3218–3357 (NH). H-NMR: δ 2.00–2.05 (quin, 2H, CH2CH2CH2),
2.34–2.38 (m, 0.7H, CH2CO), 2.80 (ddd, 1.3H, J = 4 Hz, J = 8 Hz, CH2CO), 3.29–3.36 (m, 2H, SCH2,
overlaped with DMSO), 7.39–7.69 (m, 5H, Ar-H), 7.97 (s, 0.65H, H-C=N), 8.15 (s, 0.35H, H-C=N),
11.31 (s, 0.62H, CONH), 11.43 (s, 0.32H, CONH) ppm. 13C-NMR: δ 24.06, 24.64 (CH2CH2CH2), 30.76,
32.64 (CH2CO), 33.51, 33.69 (SCH2), 126.61, 126.93, 128.75, 129.64, 129.87, 134.20, 134.28, 142.67,
145.93 (Ar-C), 164.86, 164.98, 167.63 (C=N), 167.63, 173.40 (C=O) ppm. EI MS (m/z): 526.50 (M+).
Anal. Calcd for C24H26N6O2S3: C 54.73; H 4.98; N 15.96. Found: C 54.95; H 5.09; N 15.78.
4,4′-(1,3,4-Thiadiazol-2,5-diyl)bis-(sulfanediyl)bis-(N′-(4-fluorobenzylidene)butane-hydrazide (24). This
compound was obtained as colorless crystals, Yield 91%; m.p. 154–155 °C. IR (υ, cm−1): 1672 (C=N),
1704 (C=O), 3080 (Ar-H), 3254–3358 (NH). 1H-NMR: δ 1.91–2.00 (m, 1.5H, CH2CH2CH2), 2.26–2.30
(m, 0.5H, CH2CH2CH2), 2.71 (ddd, 1H, J = 4 Hz, J = 8 Hz, CH2CO), 3.19–3.37 (m, 3H, CH2CO, SCH2
,
overlaped with DMSO), 7.21 (ddd, 1.5H, J = 8 Hz, 12 Hz, Ar-H), 7.30 (dd, 0.5H, J = 8 Hz, J = 12 Hz,
Ar-H), 7.59–7.67 (m, 1.5H, Ar-H), 7.85–7.88 (m, 1H, Ar-H, H-C=N), 8.07 (s, 0.25H, H-C=N), 8.64 (s,
13
0.25H, H-C=N), 11.23 (s, 0.65H, CONH), 11.36 (s, 0.35H, CONH) ppm. C-NMR: δ 24.06, 24.64
(CH2CH2CH2), 30.65, 30.75 (CH2CO), 33.50, 33.66 (SCH2), 130.38, 130.61, 130.70, 130.81, 130.84,
141.52, 144.82 (Ar-C), 160.42, 161.57, 164.97, 165.06 (C=N), 167.65, 173.38 (C=O) ppm. EI MS (m/z):
562.83 (M+). Anal. Calcd for C24H24F2N6O2S3: C 51.23; H 4.30; N 14.94. Found: C 51.42; H 4.39;
N 14.98.
4,4′-(1,3,4-Thiadiazol-2,5-diyl)bis-(sulfanediyl)bis-(N′-(4-trifluoromethylbenzyli-dene)butanehydrazide (25).
This compound was obtained as colorless crystals, Yield 94% yield; m.p. 185–186 °C. IR (υ, cm−1):
1648 (C=N), 1704 (C=O), 3094 (Ar-H), 3229–3342 (NH). 1H-NMR: δ 1.99–2.09 (m, 2H, CH2CH2CH2),