Page 9 of 13
RSC Advances
DOI: 10.1039/C5RA12925G
3-Methyl-2-((pyridine-2-yl-methylene)hydrazono)-2,3-dihy
drobenzo[d]thiazole (17h): Orange colour solid (187 mg, 70%); 60 ono)-2,3-dihydrobenzo[d] thiazole (17n): Yellow solid (211
1H NMR (400 MHz, DMSO-d6): mg, 78%); 1H NMR (400 MHz, DMSO-d6)
3.68 (s, 3H, NCH3), 7.21 (t, J 2.50 (s, 3H, CH3),
3-Methyl-2-(((4-methyl-1H-imidazol-5yl)methylene)hydraz
δ
δ
= 8 Hz, 1H, ArH), 7.39-7.47 (m, 2H, ArH), 7.72-7.79 (m, 2H,
ArH), 8.23 (d, J = 8 Hz, 1H, ArH), 8.34 (t, J = 8 Hz, 1H, ArH),
8.53 (s, 1H, N=CH), 8.77(d, J = 8Hz, 1H, ArH); 13C NMR (100
3.59 (s, 3H, NCH3) 7.13 (t, J = 8 Hz, 1H, ArH), 7.33-7.38 (m,
2H, ArH), 7.66 (d, J = 8 Hz, 1H, ArH), 8.41 (s, 1H, N=CH), 9.07
5
(s, 1H, ArH); 13C NMR (100 MHz, DMSO-d6):
δ 10.40, 31.50,
MHz, DMSO-d6)
δ
31.33, 111.71, 122.84, 123.05, 123.29,
65 110.93, 122.55, 123.82, 124.83, 127.10, 129.79, 134.48, 140.58,
141.14, 167.89; HRMS (+ESI) m/z calculated for C13H13N5S
271.0892, Found 294.0782 [M+Na]+.
123.99, 125.86, 127.35, 140.96, 143.23, 145.56, 170.38; HRMS
(+ESI) m/z calculated for C14H12N4S 268.0782, Found 269.0867
10 [M+H]+.
3-Methyl-2-(((4-methylthiazol-2- yl)methylene)hydrazono)
2-(3-Methylbenzo[d]thiazol-2(3H)ylidene) hydrazono)
2,3-dihydrobenzo[d]thiazole (17o): Pale yellow solid (237 mg,
methyl)quinolin-8-ol (17i): Fine orange solid (263 mg, 79%); 1H 70 75%); 1H NMR (400 MHz, DMSO-d6)
δ 2.46 (s, 3H, CH3), 3.79
NMR (400 MHz, DMSO-d6):
δ
3.71 (s, 3H, NCH3), 7.21 (t, J = 8
(s, 3H, NCH3), 7.13-7.21 (m, 1H, ArH), 7.33-7.44 (m, 2H, ArH),
7.53 (s, 1H, ArH), 7.69 (d, J = 8 Hz, 1H, ArH), 8.08 (s, 1H,
Hz, 1H, ArH),7.37-7.48 (m, 5H, ArH), 7.55-7.61 (m, 1H, ArH),
15 7.74 (d, J = 8 Hz, 1H, ArH), 8.27 (d, J = 8 Hz, 1H, ArH), 8.70 (s,
1H, ArH), 8.72 (s, 1H, N=CH); 13C NMR (100 MHz, DMSO-
N=CH); 13C NMR (100 MHz, DMSO-d6):
δ
16.31, 31.78,
110.95, 120.00, 122.59, 123.65, 126.73, 140.40, 141.61, 151.70,
d6) δ 31.95, 111.66, 118.66, 123.05, 123.26, 124.08, 127.34, 129. 75 155.33; HRMS (+ESI) m/z calculated for C13H12N4S2 288.0503,
42, 141.07; HRMS (+ESI) m/z calculated for C18H14N4OS
Found 311.0397 [M+Na]+.
2-Hydroxy-5-(((3-methylbenzo[d]thiazol-2(3H)-ylidene)
334.0888, Found 335.0982 [M+H]+.
20
2-((2-Chloroquinolin-3-yl)methylene)hydrazono)-3-methyl-
2,3dihydrobenzo[d]thiazole (17j): Yellow solid (246 mg, 70%);
hydrazono)methyl)benzoic acid (17p): Yellow colour (258 mg,
1
79%); H NMR (400 MHz, DMSO-d6):
δ 3.61 (s, 3H, NCH3),
1H NMR (400 MHz, DMSO-d6):
δ 3.62 (s, 3H, NCH3), 7.14-7.17 80 7.06 (d, J = 8 Hz, 1H, ArH) 7.12-7.14 (m, 1H, ArH),7.33-7.38
(m, 1H, ArH), 7.35-7.40 (m, 2H, ArH), 7.68 (d, J = 8 Hz, 1H,
ArH), 7.97-8.01 (m, 1H, ArH), 8.52 (s, 1H, N=CH), 8.69 (d, J =
(m, 2H, ArH), 7.68 (d, J = 8 Hz, 1H, ArH), 7.91 (dd, J = 4 Hz, 10
Hz, 1H, ArH), 7.90. (d, J = 8 Hz, 1H, ArH), 8.17 (s, 1H, OH),
8.44 (s, 1H, N=CH); 13C NMR (100 MHz, DMSO-d6): δ 31.17,
110.98, 113.87, 118.35, 122.98, 123.89, 126.52, 127.13, 129.92,
85 134.25, 141.17, 151.64, 162.86, 166.76, 171.97; HRMS (+ESI)
m/z calculated for C16H13N3O3S 327.0677, Found 328.0765
[M+H]+.
25 8 Hz, 1H, ArH), 8.84 (d, J = 8Hz, 1H, ArH), 9.08 (s, 1H, ArH);
13C NMR (100 MHz, DMSO-d6)
δ
31.63, 111.24, 122.85, 122.
93, 123.84, 127.15,127.19,134.20, 140.32, 141.06, 142.26, 143.1,
147.01, 169.47; HRMS (+ESI) m/z calculated for C18H13ClN4S
352.0549, Found 353.0635 [M+H]+.
30
3-Methyl-2-(pyridine-3-ylmethylene)hydrazono)-2,3-
dihydrobenzo[d]thiazole (17k):Yellow solid (174 mg, 65%); 1H
2-((4-Chlorobenzylidene)hydrazono)-5-methoxy-3-methyl-
2,3-dihydrobenzo[d]thiazole (17q): Yellow colour solid (235
NMR (400 MHz, DMSO-d6):
δ
3.62 (s, 3H, NCH3), 7.35-7.38 90 mg 71%); 1H NMR (400 MHz , DMSO-d6):
δ
3.60 (s, 3H,
NCH3), 3.82 (s, 3H, OCH3), 6.73-6.75 (dd, J = 2.4 Hz, 8 Hz, 1H,
ArH) 6.96-6.97 (d, J = 2.4 Hz, 1H, ArH),7.50-7.53 (m, 3H,
ArH), 7.75-7.77 (d, J = 8 Hz, 2H, ArH), 8.43 (s, 1H, N=CH); 13
NMR (100 MHz, DMSO-d6): 31.81, 56.14, 97.71, 109.03,
128.29, 129.23, 131.95, 135.95, 141.20, 147.33, 147.51, 168.82; 95 114.88, 123.40, 129.10, 129.36, 134.75, 142.32, 151.24, 159.56,
(m, 2H, ArH), 7.66-7.71 (m, 2H, ArH), 7.85 (t, J = 8 Hz, 1H,
ArH), 7.97 (d, 1H, ArH), 8.17 (s, 1H, ArH), 8.70 (s, 1H, N=CH),
35 8.89 (d, J = 8 Hz, 1H, ArH); 13C NMR (100 MHz, DMSO-d6):
δ
C
31.61, 111.05, 122.71, 122.83, 123.99, 127.17, 127.40, 128.18,
δ
HRMS (+ESI) m/z calculated for C14H12N4S 268.0783, Found
269.0869 [M+H]+.
2-(4-Bromoindolin-3-ylidene)hydrazono)-3-methyl-2,3-
168.63; HRMS (+ESI) calculated for C16H14ClN3OS 331.0546,
Found 332.0633 [M+H]+
5-Methoxy-3-methyl-2-((3,4,5-trimethoxybenzylidene)
40
1
dihydrobenzo[d]thiazole (17l): White solid (311 mg, 81%); H
hydrazono)-2,3-dihydrobenzo[d]thiazole (17r): Light yellow
NMR (400 MHz, DMSO-d6):
δ
3.68 (s, 3H, NCH3), 7.16-7.20 100 solid (301 mg, 85%); 1H NMR (400 MHz, DMSO-d6):
δ
3.61 (s,
(m, 1H, ArH), 7.36-7.43 (m, 3H, ArH), 7.47(d, J = 8 Hz, 1H,
ArH), 7.79 (d, J = 8 Hz 1H, ArH), 7.94 (d, J = 4 Hz, 1H, ArH),
3H, NCH3), 3.71 (s, 3H, OCH3), 3.83 (s, 6H, OCH3), 6.72-6.75
(dd, J = 4 Hz, 8 Hz, 1H, ArH) 6.96-6.97 (d, J = 2 Hz, 1H, ArH),
7.08 (s, 2H, ArH), 7.53-7.55 (d, J = 8 Hz, 1H, ArH), 8.37 (s, 1H,
N =CH); 13C NMR (100 MHz, DMSO-d6): δ 31.85, 56.14, 60.60,
45 8.40 (d, J = 4 Hz, 1H, ArH), 8.71 (s, 1H, N=CH);13C NMR (100
MHz, DMSO-d6)
δ 32.15, 111.12, 111.79, 113.87, 114.59,
122.76, 123.17, 123.73, 124.54, 125.73, 126.43, 127.30, 133.16, 105 97.65, 104.79, 108.99, 114.93, 123.42, 130.64, 139.64, 142.38,
136.37, 141.29, 149.49, 164.44; HRMS (+ESI) m/z calculated for
152.41, 153.59, 159.56, 167.92; HRMS (+ESI) m/z calculated for
C17H13BrN4S 386.0044, Found 387.0091 [M+H] +.
C19H21N3O4S 387.1252, Found 388.1337 [M+H]+
50
3-Methyl-2-((thiophen-2-ylmethylene)hydrazono)-2,3-
dihydrobenzo[d]thiazole (17m): Light Green Solid (218 mg,
2-((2-Chloroquinolin-3-yl)methylene)hydrazono)-5-
methoxy-3-methyl-2,3-dihydrobenzo[d]thiazole (17s): Yellow
80%; 1H NMR (400 MHz, DMSO-d6)
δ
3.59 (s, 3H, NCH3), 110 solid (298 mg, 78%); 1H NMR (400 MHz, DMSO-d6):
δ
3.65 (s,
7.11-7.15 (m, 2H, ArH), 7.32-7.38 (m, 2H, ArH), 7.44 (d, J = 4
Hz, 1H, ArH), 7.63-7.67 (m, 2H, ArH), 8.60 (s, 1H, N=CH); 13
55 NMR (100 MHz, DMSO-d6): 30.98, 110.11, 121.83, 122.27,
123.54, 126.46, 127.75, 128.33, 129.98, 139.75, 140.83, 146.76,
3H, NCH3), 3.84 (s, 3H, OCH3), 6.78-6.81 (dd, J = 4 Hz, 12 Hz,
C
1H, ArH), 7.04-7.05 (d, J = 4 Hz, 1H, ArH) 7.57-7.68 (m, 2H,
ArH), 8.14-8.20 (m, 2H, ArH), 8.41 (s, 1H, N =CH), 8.72- 8.73
(d, J = 4, 1H, ArH); 13C NMR (100 MHz, DMSO-d6) 31.22,
δ
165.80; HRMS (+ESI) m/z calculated for C13H11N3S2 273.0394, 115 55.76, 97.43, 108.75, 122.79, 126.89, 127.66, 127.75, 128.66,
Found 274.0463 [M+H]+.
131.39, 135.42, 146.76, 147.01, 148.42, 159.25, 169.34; HRMS
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