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(2C); 128.7; 130.8; 136.3; 144.7; 153.1; 156.8. HRMS (DCI, CH4) m/
z calcd for C15H15N2O3 [M+H]+: 271.1083, found: 271.1075.
4.2.19. (E)-4-((2-(Benzo[d]thiazol-2-yl)hydrazono)methyl)-2-
methoxyphenol (4e).28
Light yellow solid, yield: 99%, mp: 198.5–200.5 °C. IR (neat)
4.2.13. (E)-Benzyl 2-(2,4-Dihydroxy-5-methoxybenzylidene)
m .
max: 3488, 1624 cmꢀ1 1H NMR (300 MHz, DMSO-d6) d: 3.83
hydrazinecarboxylate (7c)
(s, 3H); 6.83 (d, J = 8.1 Hz, 1H); 7.05–7.11 (m, 2H); 7.25–7.30
(m, 2H); 7.40 (d, J = 8.1 Hz, 1H); 7.75 (d, J = 7.4 Hz, 1H); 8.02
(s, 1H); 9.47 (s, 1H); 12.06 (br s, 1H). 13C NMR (75 MHz,
DMSO-d6) d: 55.4; 109.1; 115.5; 117.4; 120.9; 121.3; 121.4;
125.7; 125.8; 129.1; 144.4; 147.9; 148.5; 166.7. HRMS (DCI,
CH4) m/z calcd for C15H14N3O2S [M+H]+: 300.0807, found:
300.0814.
Colorless solid, yield: 99%, mp: 193–195 °C. IR (neat) mmax
:
3511, 3195, 1699 cmꢀ1 1H NMR (300 MHz, DMSO-d6) d: 3.70 (s,
.
3H); 5.16 (s, 2H); 6.34 (s, 1H); 6.97 (s, 1H); 7.36–7.40 (m, 5H);
8.11 (s, 1H); 9.55 (s, 1H); 10.45 (s, 1H); 11.22 (s, 1H). 13C NMR
(75 MHz, DMSO-d6) d: 56.2; 65.9; 103.6; 109.3; 111.9; 128.0;
128.4 (2C); 136.5; 141.2; 145.2; 149.7; 152.4; 153.1. HRMS (DCI,
CH4) m/z calcd for C16H17N2O5 [M+H]+: 317.1137, found: 317.1127.
4.2.20. (E)-5-((2-(Benzo[d]thiazol-2-yl)hydrazono)methyl)-3-
4.2.14. (E)-Benzyl 2-(4-hydroxy-3,5-dimethoxybenzylidene)-1-
methoxybenzene-1,2-diol (5e).29
methylhydrazinecarboxylate hydrochloride (1d)
Grey solid, yield: 74%, mp: 262 °C. IR (neat)
mmax: 3473, 3247,
Yellow solid, yield: 96%, mp: 134.5–135.5 °C. IR (neat) mmax
:
1600 cmꢀ1 1H NMR (300 MHz, DMSO-d6) d: 6.77 (d, J = 8.1 Hz,
.
3540, 1703 cmꢀ1 1H NMR (300 MHz, DMSO-d6) d: 3.34 (s, 3H);
.
1H); 6.91 (dd, J = 1.95, 8.1 Hz, 1H); 7.08 (ddd, J = 1.1, 7.3, 7.8 Hz,
1H); 7.18 (d, J = 1.95 Hz, 1H); 7.28 (ddd, J = 1.2, 7.3, 8.0 Hz, 1H);
7.40 (d, J = 7.5 Hz, 1H); 7.74 (d, J = 7.8 Hz, 1H); 7.95 (s, 1H); 9.21
(s, 1H); 9.36 (s, 1H); 12.0 (s, 1H). 13C NMR (75 MHz, DMSO-d6) d:
112.4; 115.6; 117.4; 119.9; 121.2; 121.4; 125.7; 125.8; 129.2;
144.6; 145.6; 147.6; 166.7. HRMS (DCI, CH4) m/z calcd for C14H12-
N3O2S [M+H]+: 286.0650, found: 286.0651.
3.78 (s, 6H); 5.24 (s, 2H); 7.01 (s, 2H); 7.35–7.48 (m, 5H); 7.81 (s,
1H). 13C NMR (75 MHz, DMSO-d6) d: 30.9; 55.7; 66.9; 104.3;
125.3; 127.2; 127.8; 128.3; 136.6; 137.1; 140.9; 147.9; 153.8.
HRMS (DCI, CH4) m/z calcd for C18H21N2O5 [M+H]+: 345.1450,
found: 345.1440.
4.2.15. (E)-Benzyl 1-methyl-2-(3,4,5-trimethoxybenzylidene)
hydrazinecarboxylate hydrochloride (2d)
4.2.21. (E)-4-((2-(Benzo[d]thiazol-2-yl)-2-methylhydrazono)
Yellow solid, yield: 93%, mp: 99–101 °C. IR (neat) mmax
:
methyl)-2,6-dimethoxyphenol (1f)
1710 cmꢀ1 1H NMR (300 MHz, DMSO-d6) d: 3.35 (s, 3H); 3.69 (s,
.
Brown solid, yield: 96%, mp: 138–139 °C. IR (neat)
mmax: 3152,
3H); 3.80 (s, 6H); 2.25 (s, 2H); 7.05 (s, 2H); 7.34–7.48 (m, 5H);
7.85 (s, 1H). 13C NMR (75 MHz, DMSO-d6) d: 30.9; 55.6; 60.0;
67.0; 103.9; 127.2; 127.8; 128.3; 130.5; 136.5; 138.5; 140.1;
152.9; 153.8. HRMS (DCI, CH4) m/z calcd for C19H23N2O5 [M+H]+:
359.1607, found: 359.1605.
1600 cmꢀ1 1H NMR (300 MHz, DMSO-d6) d: 3.69 (s, 3H); 3.84 (s,
.
6H); 7.06 (s, 2H); 7.13 (ddd, J = 1.1, 7.7, 7.8 Hz, 1H); 7.31 (ddd,
J = 1.2, 7.3, 8.0 Hz, 1H); 7.58 (d, J = 7.5 Hz, 1H); 7.82 (dd, J = 0.8,
7.8 Hz, 1H); 7.93 (s, 1H); 8.85 (br s, 1H). 13C NMR (75 MHz,
DMSO-d6) d: 32.4; 55.9; 104.2; 119.4; 121.2; 121.8; 124.7;
125.7; 131.5; 137.4; 139.6; 148.1; 151.8; 168.5. HRMS (DCI,
CH4) m/z calcd for C17H18N3O3S [M+H]+: 344.1069, found:
344.1062.
4.2.16. (E)-Benzyl 2-(4-hydroxy-3-methoxybenzylidene)-1-
methylhydrazinecarboxylate hydrochloride (4d)
Yellow solid, yield: 98%, mp: 91–92 °C. IR (neat)
mmax: 3548,
3518, 1694 cmꢀ1 1H NMR (300 MHz, DMSO-d6) d: 3.33 (s, 3H);
.
4.2.22. (E)-2-(1-Methyl-2-(3,4,5-trimethoxybenzylidene)
3.78 (s, 3H); 5.24 (s, 2H); 6.82 (d, J = 8.1 Hz, 1H); 7.11 (dd, J = 1.7,
8.1 Hz,1H); 7.31 (d, J = 1.7 Hz, 1H); 7.32–7.47 (m, 5H); 7.81 (s,
1H). 13C NMR (75 MHz, DMSO-d6) d: 30.9; 55.2; 66.9; 109.3;
115.4; 121.1; 126.4; 127.3; 127.8; 128.3; 136.6; 140.9; 147.7;
148.2; 153.9. HRMS (DCI, CH4) m/z calcd for C17H19N2O4 [M+H]+:
315.1345, found: 315.1338.
hydrazinyl)benzo[d]thiazole (2f)
Colorless solid, yield: 61%, mp: 174–175.5 °C. IR (neat) mmax
:
1595, 1575 cmꢀ1 1H NMR (300 MHz, DMSO-d6) d: 3.70 (s, 3H);
.
3.72 (s, 3H); 3.86 (s, 6H); 7.10 (s, 2H); 7.15 (ddd, J = 1.1, 7.3,
7.8 Hz, 1H); 7.32 (ddd, J = 1.2, 7.3, 7.9 Hz, 1H); 7.60 (d, J = 8 Hz,
1H); 7.83 (dd, J = 0.7, 7.8 Hz, 1H); 7.96 (s, 1H). 13C NMR
(75 MHz, DMSO-d6) d: 32.4; 55.7; 60.0; 103.8; 119.5; 121.2;
122.0; 125.7; 129.9; 131.6; 138.6; 138.9; 151.7; 153.1; 168.4.
HRMS (ESI) m/z calcd for C18H20N3O3S [M+H]+: 358.1225, found:
358.1221.
4.2.17. (E)-2-(2-(3,4,5-Trimethoxybenzylidene)hydrazinyl)
benzo[d]thiazole (2e)
Yellow solid, yield: 99%, mp: 196–198 °C. IR (neat) mmax
:
1626 cmꢀ1 1H NMR (300 MHz, DMSO-d6) d: 3.70 (s, 3H); 3.84
.
(s, 6H); 7.02 (s, 2H); 7.10 (m, 1H); 7.29 (m, 1H); 7.42
(m, 1H); 7.78 (d, J = 7.7 Hz, 1H), 8.06 (s, 1H); 12.29 (br s, 1H).
13C NMR (75 MHz, DMSO-d6) d: 55.9; 60.1; 103.8; 117.6;
121.5; 121.6; 125.8; 129.0; 129.9; 138.8; 143.9; 153.2; 167.1.
HRMS (ESI) m/z calcd for C17H18N3O3S [M+H]+: 344.1069, found:
344.1072.
4.2.23. (E)-4-((2-(Benzo[d]thiazol-2-yl)-2-methylhydrazono)
methyl)-2-methoxyphenol (4f)
Yellow solid, yield: 93%, mp: 174.5–175.5 °C. IR (neat) mmax
:
3488, 1693 cmꢀ1 1H NMR (300 MHz, DMSO-d6) d: 3.68 (s, 3H);
.
3.85 (s, 3H); 6.86 (d, J = 8.1 Hz, 1H); 7.13 (ddd, J = 1.2, 7.3, 8.5 Hz,
1H); 7.19 (dd, J = 1.8, 8.1 Hz, 1H); 7.31 (ddd, J = 1.3, 7.3, 8.6 Hz,
1H); 7.35 (d, J =1.8 Hz, 1H); 7.57 (ddd, J = 0.5, 1.1, 8.0 Hz, 1H);
7.81 (ddd, J = 0.5, 1.2, 7.8 Hz, 1H); 7.92 (s, 1H); 9.48 (br s, 1H).
13C NMR (75 MHz, DMSO-d6) d: 32.3; 55.4; 109.4; 115.6; 119.4;
120.9; 121.1; 121.7; 125.7; 125.9; 131.5; 139.5; 147.8; 148.4;
151.8; 168.5. HRMS (DCI, CH4) m/z calcd for C16H16N3O2S
[M+H]+: 314.0963, found: 314.0978.
4.2.18. (E)-4-((2-(Benzo[d]thiazol-2-yl)hydrazono)methyl)
benzene-1,2-diol (3e)
Brown solid, yield: 91%. mp: 241 °C. IR (neat)
mmax: 3403, 3307,
1612 cmꢀ1 1H NMR (300 MHz, DMSO-d6) d: 3.81 (s, 3H); 6.79 (d,
.
J = 1.7 Hz, 1H); 6.83 (d, J = 1.7 Hz, 1H); 7.08 (ddd, J = 1.2, 7.7,
8.3 Hz, 1H); 7.27 (ddd, J = 1.2, 7.7, 8.3 Hz, 1H); 7.40 (d, J = 7.6 Hz,
1H); 7.74 (d, J = 7.6 Hz, 1H); 7.94 (s, 1H); 8.72 (s, 1H); 9.17 (s,
1H). 13C NMR (75 MHz, DMSO-d6) d: 55.8; 102.5; 107.3; 117.4;
121.2; 121.4; 124.6; 125.8; 129.1; 136.3; 144.7; 145.9; 148.4;
150.0; 166.7. HRMS (DCI, CH4) m/z calcd for C15H14N3O3S
[M+H]+: 316.0756, found: 316.0748.
4.2.24. (E)-3-(4-Hydroxy-3,5-dimethoxybenzylideneamino)-2-
thioxothiazolidin-4-one (1g)
Yellow solid, yield: 70.5%, mp: 175–177 °C. IR (neat)
1733, 1616, 1588 cmꢀ1 1H NMR (300 MHz, DMSO-d6) d: 3.82 (s,
6H); 4.35 (s, 2H); 7.19 (s, 2H); 8.48 (s, 1H); 9.45 (s, 1H). 13C NMR
mmax: 3486,
.