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5.2.42. 1-(Benzodioxol-5-ylmethylene)-2-(4-(4-fluorophenyl)
thiazol-2-yl)hydrazine (47)
7.12e7.15 (m, 1H, pyridine), 7.30 (s, 1H, C5H-thiazole), 7.38e7.41 (m,
1H, pyridine), 7.50e7.52 (m, 1H, pyridine), 8.00e8.10 (m, 3H, Ar),
8.63e8.65 (m, 1H, pyridine) 11.60 (bs, 1H, NH, D2O exch.).
Yield 75%; mp 204e205 ꢁC, purified by chromatography: SiO2,
ethyl acetate/hexane 1/2; 1H NMR (DMSO-d6) 6.07 (s, 2H, OCH2O),
6.95e6.97 (m,1H, Ar), 7.09e7.11 (m,1H, C5H-thiazole), 7.20e7.27 (m,
4H, Ar), 7.86e7.89 (m, 2H, Ar), 7.95 (s, 1H, N]CH), 12.00 (bs, 1H, NH,
D2O exch.).
5.2.51. 1-(Pyridin-3-ylmethylene)-2-(4-(2,4-difluorophenyl)
thiazol-2-yl)hydrazine (56)
Yield 92%; mp 209e210 ꢁC; purified by chromatography: SiO2,
ethyl acetate/hexane 3/1; 1H NMR (DMSO-d6) 7.12e7.20 (m, 1H,
pyridine), 7.24 (s, 1H, C5H-thiazole), 7.30e7.38 (m, 1H, pyridine),
7.43e7.50 (m, 1H, Ar), 7.98e8.04 (m, 2H, Ar), 8.05e8.07 (m, 1H,
pyridine), 8.54e8.55 (m, 1H, pyridine), 8.80e8.83 (s, 1H, N]CH),
12.45 (bs, 1H, NH, D2O exch.).
5.2.43. 1-(1-(2-Oxo-2H-chromen-3-yl)ethylidene)-2-(4-(4-
fluorophenyl)thiazol-2-yl)hydrazine (48)
Yield 96%; mp 221e223 ꢁC; 1H NMR (DMSO-d6) 2.27 (s, 3H, CH3),
7.28e7.39 (m, 4H, Ar), 7.42 (s, 1H, C5H-thiazole), 7.61e7.75 (m, 4H,
Ar), 8.20 (s, 1H, C4H-coumarin), 11.30 (bs, 1H, NH, D2O exch.).
5.2.52. 1-(1-(Pyridin-3-yl)ethylidene)-2-(4-(2,4-difluorophenyl)
thiazol-2-yl)hydrazine (57)
5.2.44. 1-(Furan-2-ylmethylene)-2-(4-(2,4-difluorophenyl)thiazol-
2-yl)hydrazine (49)
Yield 95%; mp 235e236 ꢁC; purified by chromatography: SiO2,
ethyl acetate/hexane 3/1; 1H NMR (DMSO-d6) 2.31 (s, 3H, CH3),
7.17e7.20 (m, 1H, pyridine), 7.27 (s, 1H, C5H-thiazole), 7.30e7.35 (m,
1H, pyridine), 7.47e7.50 (m, 1H, Ar), 7.60e7.63 (m, 1H, Ar), 7.67e
7.70 (m, 1H, Ar), 7.98e8.00 (m, 1H, pyridine), 8.55e8.60 (m, 1H,
pyridine), 11.50 (bs, 1H, NH, D2O exch.).
Yield 75%; mp 179e180 ꢁC, purified by chromatography: SiO2,
ethyl acetate/hexane 1/1; 1H NMR (DMSO-d6) 6.59e6.62 (m, 1H,
furan), 6.80e6.82 (m, 1H, furan), 7.16e7.18 (m, 1H, furan), 7.20 (s,1H,
C5H-thiazole), 7.31e7.38 (m,1H, Ar), 7.79e7.80 (m,1H, Ar), 7.94e7.98
(m, 1H, Ar), 7.98e8.06 (m, 1H, N]CH), 11.70 (bs, 1H, NH, D2O exch.).
5.2.45. 1-(1-(Furan-2-yl)ethylidene)-2-(4-(2,4-difluorophenyl)
thiazol-2-yl)hydrazine (50)
5.2.53. 1-(Pyridin-4-ylmethylene)-2-(4-(2,4-difluorophenyl)
thiazol-2-yl)hydrazine (58)
Yield 69%; mp 190e191 ꢁC, purified by chromatography: SiO2,
ethyl acetate/hexane 1/1; 1H NMR (DMSO-d6) 2.24 (s, 3H, CH3),
6.55e6.63 (m,1H, furan), 6.80e6.90 (m,1H, furan), 7.15e7.25 (m,1H,
furan), 7.27 (s, 1H, C5H-thiazole), 7.30e7.45 (m, 1H, Ar), 8.75e8.85
(m, 1H, Ar), 8.05e8.20 (m, 1H, Ar), 10.75 (bs, 1H, NH, D2O exch.).
Yield 90%; mp 224e225 ꢁC; purified by chromatography: SiO2,
ethyl acetate/hexane 2/1; 1H NMR (DMSO-d6) 7.33e7.35 (m,1H, Ar),
7.93e7.94 (m, 2H, pyridine), 8.07 (s, 1H, C5H-thiazole), 8.13e8.16
(m, 2H, Ar), 8.54 (s, 1H, N]CH), 8.74e8.75 (m, 2H, pyridine),
11.94 (s, 1H, NH, D2O exch.).
5.2.46. 1-(Thiophen-2-ylmethylene)-2-(4-(2,4-difluorophenyl)
thiazol-2-yl)hydrazine (51)
5.2.54. 1-(1-(Pyridin-4-yl)ethylidene)-2-(4-(2,4-difluorophenyl)
thiazol-2-yl)hydrazine (59)
Yield 75%; mp 174e175 ꢁC, purified by chromatography: SiO2,
ethyl acetate/hexane 1/1; 1H NMR (DMSO-d6) 7.09e7.23 (m, 3H,
thiophene), 7.30e7.36 (m, 1H, Ar), 7.37 (s, 1H, C5H-thiazole), 7.58e
7.61 (m, 1H, Ar), 7.98e8.01 (m, 1H, Ar), 8.25 (s, 1H, N]CH), 11.90
(bs, NH, D2O exch.).
Yield 91%; mp 229e230 ꢁC; purified by chromatography: SiO2,
ethyl acetate/hexane 2/1; 1H NMR (DMSO-d6) 2.31 (s, 3H, CH3), 7.88
(s, 1H, C5H-thiazole), 8.08e8.09 (d, J3-2 ¼ 7.8 Hz, 2H, pyridine),
8.23e8.27 (m, 1H, Ar), 8.50e8.53 (m, 1H, Ar), 8.64e8.65 (d, J2-
¼ 7.8 Hz, 2H, pyridine), 8.68e8.70 (m, 1H, Ar), 10.52 (s, 1H, NH,
3
D2O exch.).
5.2.47. 1-(1-(Thiophen-2-yl)ethylidene)-2-(4-(2,4-difluorophenyl)
thiazol-2-yl)hydrazine (52)
5.2.55. 1-(Naphthalen-1-ylmethylene)-2-(4-(2,4-difluorophenyl)
thiazol-2-yl)hydrazine (60)
Yield 97%; mp 189e190 ꢁC; purified by chromatography: SiO2,
ethyl acetate/hexane 1/1; 1H NMR (DMSO-d6) 2.33 (s, 3H, CH3),
7.04e7.06 (m, 1H, thiophene), 7.17e7.20 (m, 2H, thiophene), 7.31e
7.38 (m, 2H, Ar), 7.51 (s, 1H, C5H-thiazole), 8.08e8.10 (m, 1H, Ar),
11.37 (bs, 1H, NH, D2O exch.).
Yield 78%; mp 153e155 ꢁC, purified by chromatography: SiO2,
ethyl acetate/hexane 1/3; 1H NMR (DMSO-d6) 7.15e7.18 (m, 1H,
Ar), 7.25 (s, 1H, C5H-thiazole), 7.34e7.37 (m, 1H, Ar), 7.56e7.57 (m,
1H, Ar), 7.59e7.61 (m, 1H, Ar), 7.64e7.67 (m, 1H, Ar), 7.85e7.87
(m, 1H, Ar), 7.95e7.97 (m, 1H, Ar), 7.99e8.02 (m, 2H, Ar), 8.68
(s, 1H, N]CH), 8.74e8.76 (m, 1H, Ar), 12.37 (bs, 1H, NH, D2O
exch.).
5.2.48. 1-(1-(Thiazol-2-yl)ethylidene)-2-(4-(2,4-difluorophenyl)
thiazol-2-yl)hydrazine (53)
Yield 92%; mp 195e196 ꢁC; purified by chromatography: SiO2,
ethyl acetate/hexane 1/1; 1H NMR (DMSO-d6) 2.42 (s, 3H, CH3),
7.18e7.22 (m, 1H, Ar), 7.27 (s, 1H, C5H-thiazole), 7.65e7.77 (m, 1H,
Ar), 7.71e7.72 (d, J ¼ 3.1 Hz, 1H, thiazole), 7.84e7.85 (d, J ¼ 3.1 Hz,
1H, thiazole), 8.00e8.12 (m, 1H, Ar), 10.62 (bs, 1H, NH, D2O exch.).
5.2.56. 1-(1-(Naphthalen-2-yl)ethylidene)-2-(4-(2,4-
difluorophenyl)thiazol-2-yl)hydrazine (61)
Yield 74%; mp 187e188 ꢁC, purified by chromatography: SiO2,
ethyl acetate/hexane 1/1; 1H NMR (DMSO-d6) 2.45 (s, 3H, CH3),
7.18e7.25 (m, 2H, Ar), 7.34 (s, 1H, C5H-thiazole), 7.52e7.54 (m, 2H,
Ar), 7.90e7.93 (m, 3H, Ar), 7.96e7.98 (m, 1H, Ar), 8.08e8.10 (m, 1H,
Ar), 8.21 (s, 1H, Ar), 11.35 (bs, 1H, NH, D2O exch.).
5.2.49. 1-(1-Phenylethylidene)-2-(4-(2,4-difluorophenyl)thiazol-2-
yl)hydrazine (54)
Yield 96%; mp 205e207 ꢁC; purified by chromatography: SiO2,
ethyl acetate/hexane 1/1; 1H NMR (DMSO-d6) 2.32 (s, 3H, CH3),
7.22e7.25 (m, 3H, Ar), 7.28 (s, 1H, C5H-thiazole), 7.45e7.51 (m, 2H,
Ar), 7.77e7.80 (m, 3H, Ar), 10.40 (bs, 1H, NH, D2O exch.).
5.2.57. 1-((1H-indol-3-yl)methylene)-2-(4-(2,4-difluorophenyl)
thiazol-2-yl)hydrazine (62)
Yield 70%; mp 183e185 ꢁC, purified by chromatography: SiO2,
ethyl acetate/hexane 3/1; 1H NMR (DMSO-d6) 7.15e7.25 (m, 4H,
indole), 7.30e7.40 (m, 1H, indole), 7.43e7.44 (d, Jo ¼ 8.5 Hz, 1H, Ar),
7.78 (s, 1H, C5H-thiazole), 8.00e8.10 (m, 1H, Ar), 8.22e8.23 (d,
Jo ¼ 8.5 Hz, 1H, Ar), 8.27 (s, 1H, N]CH), 11.53 (s, 1H, NH-indole, D2O
exch.), 11.80 (bs, 1H, NH, D2O exch.).
5.2.50. 1-(1-(Pyridin-2-yl)ethylidene)-2-(4-(2,4-difluorophenyl)
thiazol-2-yl)hydrazine (55)
Yield 91%; mp 189e190 ꢁC; purified by chromatography: SiO2,
ethyl acetate/hexane 2/1; 1H NMR (DMSO-d6) 2.42 (s, 3H, CH3),