Struct Chem
( E ) - 1 - p h e n y l - 2 - ( 4 - ( t r i f l u o r o m e t h y l ) -
benzylidene)hydrazine (2)
2-(3-(trifluoromethyl)phenyl)phthalazin-1(2H)-one (8)
1H NMR (300.128 MHz, CDCl3), δ (ppm): 8.53–
8.50 (d, 1H, J = 7.5 Hz), 8.32 (s, 1 H, −CH), 8.02–
7.76 (m, 5H), 7.64–7.61 (m, 2H); 13C NMR
(75.466 MHz, CDCl3), δ (ppm): 157.0, 139.0,
134.4, 133.8, 132.2, 130.8, 129.3, 129.1, 128.8,
128.3, 127.2, 126.3, 125.4, 124.2, 123.4, 122.6;
MS C15H9F3N2O: 289 (M+-1)
1H NMR (300.12 MHz, CDCl3), δ (ppm) 7.67 (d, 1H,
J = 9 Hz), 7.56 (m, 3H), 7.28 (t, 2H, J = 9 Hz), 7.09 (d,
2H, J = 9 Hz), 6.90 (t, 1H, J = 6 Hz). 13C NMR
(75.47 MHz, CDCl3), (ppm) 144.0, 135.1, 129.4, 126.1,
125.6, 125.5, 125.4, 120.7, 112.9. 19F NMR
(300.12 MHz, CDCl3), δ (ppm) -62.5. MS: C14H11F3N2
264 (M+, 100 %); 92 (58 %).
(E)-5-methoxy-2-((2-(3-(trifluoromethyl)phenyl)-
hydrazono)methyl)phenol (9)
(E)-1-(2-bromobenzylidene)-2-(4-nitrophenyl)hydrazine (3)
1H NMR (300.12 MHz, DMSO-d6), δ (ppm) 11.50
(br, 1H), 8.23 (s, 1H), 8.04 (d, 2H, J = 9 Hz), 7.94 (d,
1H, J = 6 Hz), 7.56 (d, 1H, J = 6 Hz), 7.34 (t, 1H,
J = 6 Hz), 7.20 (t, 1H, J = 6 Hz), 7.09 (d, 2H,
J = 9 Hz). 13C NMR (75.47 MHz, DMSO-d6), (ppm)
150.8, 140.3, 139.4, 133.9, 133.7, 131.4, 128.7, 127.4,
126.8, 123.2, 112.2. MS: C13H10BrO2N3: 91 (100 %);
207 (23 %)
1H NMR (300.128 MHz, CDCl3), δ (ppm): 10.85 (s,
1H), 7.87 (s, 1H), 7.45–7.26 (m, 2H), 7.14–7.12 (m, 3H),
7.08–7.06 (d, 1H, J = 8.4 Hz), 6.55 (s, 1H), 6.51–6.48 (d,
1H, J = 8.4 Hz), 3.83 (s, 3H); MS C15H13F3N2O2: 310
(M+)
(E)-1-(3-hydroxylbenzylidene)-2-phenylhydrazine (10)
1H NMR (399.822 MHz, DMSO-d6), δ (ppm) 10.25
(s, 1H), 9.51 (br, s, 1H), 7.73 (s, 1H), 7.35–7.15 (m, 6H),
6.90–6.65 (m, 3H). MS: C13H11N2Cl 230 (M+, 100 %);
92 (63 %); 229 (M+-1, 31 %); MS: C13H12ON2: 212 (M+-
1, 100 %); 92 (33 %)
(E)-1-(3,4-dimethoxybenzylidene)-2-(2-(trifluoro-
methyl)phenyl)hydrazine (4)
1H NMR (300.12 MHz, CDCl3), δ (ppm) 7.94 (br,
1H), 7.77 (m, 2H), 7.48 (m, 2H), 7.38 (s, 1H), 7.08
(m, 1H), 6.88(m, 1H), 3.97 (s, 3H), 3.92, (s, 3H). 13C
NMR (75.47 MHz, CDCl3), (ppm) 150.2, 149.3,
140.3, 133.1, 127.7, 126.2, 126.1, 120.8, 118.7,
114.5, 110.7, 107.7, 55.9, 55.8. 19F NMR
(300.12 MHz, CDCl3), δ (ppm) -61.8. MS: C16
H15F3O2N2: 324 (M+, 100 %); 138 (23 %).
(E)-1-(2-bromobenzylidene)-2-(2-(trifluoro-
methyl)phenyl)hydrazine (5)
(E)-N,N-dimethyl-4-((2-(3-(trifluoromethyl)-
phenyl)hydrazono)methyl)aniline (11)
1H NMR (300.128 MHz, CDCl3), δ (ppm): 7.64 (s,
1H), 7.57–7.54 (m, 3H), 7.32–7.30 (m, 2H), 7.19–7.16
(d, 1H, J = 8.1 Hz), 7.13 (m, 1H), 6.71 (m, 2H), 3.00 (s,
6H). MS: C16H16F3N3: 308 (M++1)
(E)-1-(4-nitrobenzylidene)-2-(3-(trifluoro-
methyl)phenyl)hydrazine (12)
1H NMR (300.12 MHz, DMSO-d6), δ (ppm) 10.62
(br, 1H), 8.19 (d, 2H, J = 9 Hz), 7.90 (s, 1H), 7.79 (d,
1H NMR (300.12 MHz, CDCl3), δ (ppm) 8.26 (br,
1H), 8.18 (s, 1H), 8.06 (d, 1H, J = 6 Hz), 7.81 (d, 1H,
J = 6 Hz), 7.55 (m, 3H), 7.37 (m, 1H), 7.19 (t, 1H,
J = 6 Hz) 6.94 (t, 1H, J = 6 Hz). 13C NMR
(75.47 MHz, CDCl3), (ppm) 137.1,38.6, 133.2, 133.1,
130.1, 127.5, 127.2, 126.2, 119.4, 114.8. 19F NMR
(300.12 MHz, CDCl3 ), δ (ppm) -60.9. MS:
C14H9F3BrN2: 342 (M+-1, 98 %); 243 (100 %).
(E)-1-(4-(trifluoromethyl)benzylidene)-2-(3-(trifluoro-
methyl)phenyl)hydrazine (6)
2H, J = 9 Hz), 7.38 (m, 3H), 7.07 (d, 1H, J = 3 Hz). 13
C
NMR (75.47 MHz, DMSO-d6), (ppm) 145.8, 144.2,
141.4, 134.1, 128.9, 125.3, 123.1, 115.3, 115.2, 115.1,
108.3, 108.2. 19F NMR (300.12 MHz, DMSO-d6), δ
(ppm) -62.5. MS: C14H10F3O2N3: 309 (M+, 100 %).
(E)-N,N-dimethyl-4-((2-(2-(trifluoromethyl)-
phenyl)hydrazono)methyl)aniline (13)
1H NMR (300.128 MHz, CDCl3), δ (ppm): 7.80–
7.74 (m, 2H, Ar –H, 1H, −CH)), 7.58–7.55 (2H,
J = 8.7 Hz), 7.47–7.45 (m, 2H), 7.82 (m, 1H),
6.73–6.70 (d, J = 8.4 Hz), 3.01 (s, 6H); MS
C16H16F3N3: 307 (M+)
1-(diphenylmethylene)-2-phenylhydrazine (14)
1H NMR (399.822 MHz, DMSO-d6), δ (ppm): 8.75
(s, 1H), 7.61–7.57 (m, 2H), 7.41–7.25 (m, 5H), 7.22–
7.08 (m, 7H), 6.72 (m, 1H); MS C20H18N2: 272 (M+,
100 %); 77 (30 %)
1,4-bis((E)-(2-phenylhydrazono)methyl)benzene (15)
1H NMR (399.822 MHz, DMSO-d6), δ (ppm): 10.37
(s, 2H), 7.82 (s, 2H), 7.61 (s, 4H), 7.23–7.06 (m, 8H),
6.73 (m, 2H); MS C20H18N4: 196 (100 %), 92 (37 %), 77
(15 %).
1H NMR (300.12 MHz, CDCl3), δ (ppm) 8.17 (br,
1H), 7.80 (m, 4H), 7.63 (d, 2H, J = 6 Hz), 7.50 (m,
2H), 6.95 (t, 1H, J = 6 Hz). 13C NMR (75.47 MHz,
CDCl3), (ppm) 138.4, 133.7, 126.9, 126.7, 126.7,
126.1, 126.0, 125.9, 120.1, 115.3. 19F NMR
(300.12 MHz, CDCl3), δ (ppm) -60.9, −62.7. MS:
C15H10F6N2: 332 (M+, 100 %); 160 (15 %).
(E)-5-methoxy-2-((2-(4-(trifluoromethyl)phenyl)-
hydrazono)methyl)phenol (7)
1H NMR (399.822 MHz, DMSO-d6), δ (ppm): 10.51
(s, 1H), 8.10 (s, 1H), 7.49 (m, 2H), 7.15 (m, 2H), 7.01 (d,
1H), 6.46 (m, 2H), 3.85 (s, 3H). MS: C14H13F3O2N2: 310
(M+, 100 %);161 (43 %)