N. P, J.P. Dasappa, H. B et al.
Journal of Molecular Structure 1236 (2021) 130305
Table 1
The physicochemical characteristics of arylhydrazones (5a-i) and (5j-l).
SN
Comp. code
Ar-CHO
4-F-3-OC6H5 C6H3
M.P. ( °C)
Yield (%)
Mol. For.
Mol. Wt
–
1.
5a
5b
5c
5d
5e
5f
138–140
230–232
210–212
190–192
196–198
198–200
206–208
218–220
186–188
186–188
182–184
228–230
72
82
76
74
72
90
88
88
74
78
84
86
C29H25FN4O3S
C24H24N4O4S
C24H24N4O4S
C25H26N4O4S
C23H21N5O4S
C24H24N4O2S
C23H21ClN4O2S
C23H22N4O3S
C24H24N4O3S
C27H23N5O5S
C22H22N4O3S
C21H19N5O5S
528.59
464.53
464.53
478.56
463.51
432.53
452.95
434.51
448.53
529.56
422.50
453.47
–
4-OH-3–OCH3 C6H3
2.
–
3-OH-4–OCH3 C6H3
3.
–
3,4-(OCH3)2 C6H3
4.
–
4-NO2 C6H4
5.
–
6.
2-CH3 C6H4
7.
5 g
5h
5i
4-Cl-C6H4
–
4-OH C6H4
8.
–
9.
4–OCH3 C6H4
–
10.
11.
12.
5j
5-(2-NO2 C6H4)−2-furaldehyde
5k
5l
5-CH3–2-furaldehyde
5-NO2–2-furaldehyde
1H, Ar-H), 3.90(d, 2H, J = 8 Hz, CH2), 2.85(s, 3H, CH3), 2.21–2.23(d,
7.45(d, 1H, J = 8 Hz, Ar-H), 4.08–4.10(d, 2H, J = 8 Hz CH2), 2.84(s,
1H, C H), 1.11(s, 6H, CH3); 13C NMR(100 MHz), δ(ppm):162.24,
3H, CH3), 2.17–2.22(m, 1H, C H), 1.14(d, 6H, J = 8 Hz, CH3); 13C
–
–
156.89, 132.56, 132.01, 130.62, 129.87, 124.19, 123.57, 120.42,
117.89, 117.74, 117.42, 115.51, 112.62, 102.94, 77.29, 77.03, 76.78,
75.72, 28.18, 19.09; MS (m/z): 529 (M++1); Elemental Analysis:
anal. cald. (%) for C29H25FN4O3S: C: 65.89; H: 4.77; N: 10.60;
Found: C: 65.90; H: 4.75; N:10.62.
NMR (100 MHz), δ (ppm): 162.36, 134.97, 133.39, 131.67, 129.47,
129.36, 126.11, 115.82, 114.41, 102.16, 75.66, 40.76, 40.55, 40.35,
40.13, 39.93, 39.72, 39.51, 28.04, 19.12; MS (m/z): 453 (M+), 455
(M++2); Elemental Analysis: anal. cald. (%) for C23H21ClN4O2S: C:
60.99; H: 4.67; N: 12.37; Found: C:60.97; H:4.68; N:12.38.
2.4.5. (E)−2-(3-Cyano-4-isobutoxyphenyl)-N’-(4-
hydroxybenzylidene)−4-methylthiazole-5-carbohydrazide
(5 h)
2.4.2. (E)−2-(3-Cyano-4-isobutoxyphenyl)−4-methyl-N’-(4-
nitrobenzylidene)thiazole-5-carbohydrazide
(5e)
Appearance: Pale yellow solid;FT-IR(KBr, νmax, cm−1):
Appearance: Yellow solid; FT-IR (KBr, νmax, cm−1): 3166(N H),
–
–
–
≡≡
N),
3163(N H), 3041(Ar-H), 2961, 2840(C H of CH3), 2226(C
–
≡≡
3057(Ar-H), 2959, 2873(C H), 2227(C
N), 1651(C
=
O),
1656(C = O), 1604(C N), 1571(C
=
=
C); 1H NMR(400 MHz,
1606(C = N), 1580(C = C), 1521 & 1430(NO2 asym. & sym.);
–
DMSO–d6), δ(ppm): 11.73 (bs, 1H, N H), 10.07(s, 1H, OH), 8.35 (s,
1H NMR (400 MHz, DMSO–d6), δ(ppm): 11.94 (bs, 1H, N H),
–
=
1H, Ar-H), 8.29(d, 1H, J = 8 Hz, Ar-H), 8.11(s, 1H, CH N), 7.71(d,
=
8.26(d, 2H, J = 8 Hz, Ar-H), 8.19(s, 1H, CH N), 8.13–8.16(dd, 2H,
2H, J = 8 Hz, Ar-H), 7.45(d, 1H, J = 8 Hz, Ar-H), 6.99(d, 2H, Ar-H),
Ar-H), 7.93(d, 2H, Ar-H), 7.31(d, 1H, J = 8 Hz Ar-H), 3.97(d, 2H,
–
4.09(d, 2H, J = 8 Hz CH2), 2.85(s, 3H, CH3), 2.19–2.22(m, 1H, C H),
–
J = 8 Hz, CH2), 2.71(s, 3H, CH3), 2.08–2.11(m, 1H, C H), 1.03(d,
1.14(d, 6H, J = 8 Hz, CH3); 13C NMR(100 MHz), δ (ppm):168.09,
162.23, 161.45, 159.86, 144.55, 133.26, 131.62, 129.57, 126.19,
125.44, 119.42, 116.32, 115.89, 114.28, 102.01, 75.53, 40.63, 40.42,
40.01, 39.59, 39.38, 28.03, 19.15; MS (m/z): 435(M++1); Elemental
Analysis: anal. cald. (%) for C23H22N4O3S: C: 63.58; H: 5.10; N:
12.89; Found: C:63.55; H:5.12; N:12.90.
6H, J = 8 Hz, CH3); 13C NMR (100 MHz): δ (ppm): 162.34, 148.14,
140.66,133.34, 131.60, 128.57, 125.97, 124.49, 115.79, 114.28, 102.12,
75.63, 40.75, 40.55, 40.34, 40.13, 39.93, 39.71, 39.51, 28.04, 19.11;
MS (m/z): 464(M++1); Elemental Analysis: anal. cald. (%) for
C23H21N5O4S: C: 59.60; H: 4.57; N:15.11; Found: C: 59.62; H: 4.55;
N: 15.12.
2.4.6. (E)−2-(3-Cyano-4-isobutoxyphenyl)-N’-(4-
methoxybenzylidene)−4-methylthiazole-5-carbohydrazide
(5i)
2.4.3. (E)−2-(3-Cyano-4-isobutoxyphenyl)−4-methyl-N’-(2-
methylbenzylidene)thiazole-5-carbohydrazide
(5f)
Appearance: Yellow Solid; FT-IR (KBr, νmax, cm−1): 3164(N H),
–
Appearance: Pale yellow solid;FT-IR (KBr, νmax, cm−1):
–
≡≡
3041(Ar-H), 2958, 2935(C H), 2227(C
N), 1656(C
=
O),
–
–
≡≡
N),
3162(N H),
3052(Ar-H),
2959,
2873(C H),
2226(C
1604(C = N); 1H NMR(400 MHz, DMSO–d6), δ(ppm): 11.61(bs,
1655(C = O), 1605(C = N), 1588(C = C); 1H NMR(400 MHz,
–
=
1H, N H), 8.20(s, 1H, CH N), 8.15(d, 1H, J = 8 Hz, Ar-H), 8.02(s,
1H, Ar-H) 7.67(d, 2H, Ar-H), 7.32(d, 1H, J = 8 Hz, Ar-H), 7.02(d,
2H, Ar-H), 3.97(d, 2H, J = 8 Hz, CH2), 3.806(s, 3H, OCH3), 2.72(s,
–
DMSO–d6), δ(ppm): 11.62 (bs, 1H, N H), 8.45(s, 1H, Ar-H), 8.20(s,
=
1H, CH N), 8.15(d, 1H, J = 8 Hz, Ar-H), 7.89(d, 1H, J = 8 Hz,
Ar-H), 7.30–7.35(m, 3H, Ar-H), 7.25(d, 1H, J = 8 Hz, Ar-H), 3.98(d,
2H, J = 8 Hz CH2), 2.72(s, 3H, CH3), 2.42(s, 3H, CH3), 2.06–
3H, CH3), 2.06–2.10(m, 1H, C H), 1.02(d, 6H, J = 8 Hz, CH3); 13C
–
NMR(100 MHz), δ(ppm):162.31, 161.34, 133.28, 131.62, 129.36,
127.10, 126.24, 115.82, 114.95, 114.43, 102.19, 75.69, 55.82, 40.80,
40.59, 40.38, 40.17, 39.97, 39.75, 39.55, 28.05, 19.11; MS (m/z): 449
(M++1); Elemental Analysis: anal. cald. (%) for C24H24N4O3S: C:
64.27; H: 5.39; N: 12.49; Found: C:64.28; H:5.40; N:12.51.
2.12(m, 1H, C H), 1.03(d, 6H, J = 8 Hz, CH3); 13C NMR(100 MHz),
–
δ(ppm): 162.33, 137.35, 133.21, 132.48, 131.60, 131.27, 130.21,
126.75, 126.46, 126.18, 115.80, 114.44, 102.19, 75.69, 40.80, 40.59,
40.38, 40.17, 39.97, 39.76, 39.55, 28.05, 19.26, 19.11; MS (m/z):
433(M++1); Elemental Analysis: anal. cald. (%) for C24H24N4O2S:
C: 66.64; H: 5.59; N: 12.95; Found: C:66.65; H:5.61; N:12.94.
2.4.7. (E)−2-(3-Cyano-4-isobutoxyphenyl)−4-methyl-N’-((5-(2-
nitrophenyl)furan-2-yl)methylene)thiazole-5-carbohydrazide
(5j)
2.4.4. (E)-N’-(4-Chlorobenzylidene)−2-(3-cyano-4-
isobutoxyphenyl)−4-methylthiazole-5-carbohydrazide
(5 g)
Appearance: Yellow solid;FT-IR (KBr, νmax, cm−1): 3139(N H),
–
–
≡≡
N), 1651(C = O), 1604(C = N), 1525
2926(C H of CH3), 2226(C
& 1426(NO2asym. & sym.); 1H NMR (400 MHz, DMSO–d6), δ(ppm):
Appearance: Pale yellow solid;FT-IR (KBr, νmax, cm−1):
–
–
≡≡
N),
–
=
3161(N H), 3052(Ar-H), 2959, 2872(C H of CH3), 2227(C
11.79(bs, 1H, N H), 8.20(s, 1H, CH N), 8.15(d, 1H, J = 8 Hz Ar-H),
7.88–7.91(m, 3H, Ar-H), 7.69–7.73(m, 1H, Ar-H), 7.58–7.61(m, 1H,
Ar-H), 7.22(d, 1H, J = 8 Hz, Ar-H), 7.06(d, 2H, J = 8 Hz furylAr-
H), 3.95(d, 2H, J = 8 Hz CH2), 2.73(s, 3H, CH3), 2.06–2.09(m,
164 (C
=
O), 1605(C
=
N); 1H NMR(400 MHz, DMSO–d6),
–
δ(ppm):11.98(bs, 1H, N H), 8.35(s, 1H, Ar-H), 8.28–8.30(dd,
1H, Ar-H), 8.17(s, 1H, CH N), 7.87(d, 2H, Ar-H), 7.63 (d, 2H, Ar-H),
=
3