Boga et al.
2
92.0848, found 292.0847. Anal. Calcd for C17
H
12
N
2
O
3
: C,
67.35; H, 4.24; N, 4.91. Found: C, 67.31; H, 4.23; N, 4.92. IR
-1
6
9.86; H, 4.14; N, 9.58. Found: C, 69.84; H, 4.13; N, 9.60. IR
(CHCl
3
) (ν, cm ) 3571, 3410, 1599, 1504, 1164, 1080, 935, 893,
-
1
(
CHCl
,1-Bis(1-methyl-1H-benzimidazol-2-yl)-2-propen-1-ol
22): orange solid; mp 143-145 °C (from CH OH); R 0.56
) δ 3.58 (s, 6H), 5.28
d, 1H, J ) 17.0 Hz), 5.50 (d, 1H, J ) 10.0 Hz), 5.95-6.10 (br
3
) (ν, cm ) 3600, 1016, 848.
843.
1
1-(1,3-Benzothiazol-2-yl)-1-phenyl-2-propen-1-ol
(26e): white solid, mp 113-115 °C (from CH OH); R 0.32 (8:2
petroleum ether:diethyl ether); H NMR (300 MHz, CDCl ) δ
(
3
f
3
f
1
1
(
diethyl ether); H NMR (300 MHz, CDCl
3
3
(
3.85 (s, 1H, OH), 5.45 (dd, 1H, J ) 10.5 Hz, J ) 0.8 Hz), 5.55
(dd, 1H, J ) 17.1 Hz, J ) 0.8 Hz), 6.73 (dd, 1H, J ) 17.1 Hz,
J ) 10.5 Hz), 7.32-7.61 (m, 7H), 7.87 (dd, 1H, J ) 8.0 Hz, J
s, 1H, OH), 7.02 (dd, 1H, J ) 17.0 Hz, J ) 10.0 Hz), 7.25-
13
7
3
.35 (m, 6H), 7.78-7.85 (m, 2H); C NMR (75.46 MHz, CDCl )
1
3
δ 50.7, 73.3, 109.5, 116.8, 120.0, 122.5, 123.4, 137.1, 137.7,
) 1.4 Hz), 8.04 (dd, 1H, J ) 8.2 Hz, J ) 0.8 Hz); C NMR
(75.46 MHz, CDCl ) δ 79.1, 115.6, 121.7, 123.3, 125.2, 126.1,
+
1
2
40.8, 152.7; MS (70 eV, EI) m/z (%) 318 [M , 51], 301 (26),
3
1
26.4, 128.2, 128.3, 128.5, 141.1, 143.3, 152.8, 176.7; MS (70
91 (18), 170 (59), 159 (100), 133 (74), 55 (87); HRMS calcd
+
eV, EI) m/z 267 [M , 49], 250 (58), 239 (23), 224 (32), 212 (17),
90 (10), 162 (31), 135 (64), 105 (100), 77 (86), 55 (77); HRMS
calcd for C H NOS 267.0718, found 267.0720. Anal. Calcd
for C19
18 4
H N O 318.1481, found 318.1480. Anal. Calcd for
1
19 18 4
C H N O: C, 71.68; H, 5.70; N, 17.60. Found: C, 71.65; H,
-
1
5
1
.73; N, 17.63. IR (CHCl
500, 1465, 1335, 1049, 965, 893.
-(1,3-Benzothiazol-2-yl)-1-[4-(trifluoromethyl)phenyl]-
-propen-1-ol (26a): colorless oil; R 0.20 (8:2 petroleum
) δ 4.10 (s, 1H,
3
) (ν, cm ) 3617, 3402, 1656, 1614,
16 13
for C16H13NOS: C, 71.88; H, 4.90; N, 5.24. Found: C, 71.85;
H, 4.89; N, 5.22. IR (CHCl
1
-
1
3
) (ν, cm ) 3686, 3594, 3433, 1675,
591, 1492, 1320, 1068, 1026, 931, 893.
1-(1,3-Benzothiazol-2-yl)-1-(4-methoxyphenyl)-2-propen-
-ol (26f): white solid, mp 78-80 °C (from methanol); R 0.40
1
2
f
1
ether:diethyl ether); H NMR (300 MHz, CDCl
3
1
f
OH), 5.47 (d, 1H, J ) 10.9 Hz), 5.52 (d, 1H, J ) 17.5 Hz), 6.69
dd, 1H, J ) 17.5 Hz, J ) 10.9 Hz), 7.36-7.44 (m, 1H), 7.46-
1
(
3
6:4 petroleum ether:diethyl ether); H NMR (300 MHz, CDCl )
(
δ 4.04 (s, 3H), 4.29 (s, 1H, OH), 5.67 (dd, 1H, J ) 10.5 Hz, J
) 0.9 Hz), 5.78 (dd, 1H, J ) 17.1 Hz, J ) 0.9 Hz), 6.94 (dd,
7
.53 (m, 1H), 7.58-7.65 (m, 2H), 7.70-7.76 (m, 2H), 7.84-
13
7
.90 (m, 1H), 8.00-8.05 (m, 1H); C NMR (75.46 MHz, CDCl
), 116.4, 121.7, 123.3, 125.4,
), 126.3, 126.8, 130.7 (q, J )
), 135.3, 140.5, 149.3, 152.7, 176.0; MS (70 eV,
3
)
1
H, J ) 17.1 Hz, J ) 10.5 Hz), 7.13 (d, 2H, J ) 9.0 Hz), 7.55-
.65 (m, 1H), 7.65-7.75 (m, 1H), 7.74 (d, 2H, J ) 9.0 Hz), 8.10
δ 82.9, 123.8 (q, J ) 278.0 Hz, CF
3
7
1
3
25.5 (q, J ) 3.8 Hz, CH-C-CF
4.9 Hz, C-CF
3
1
3
(
d, 1H, J ) 8.0 Hz), 8.19 (d, 1H, J ) 8.2 Hz); C NMR (75.46
3
+
MHz, CDCl
3
) δ 55.2, 78.8, 113.7, 115.3, 121.6, 123.1, 125.0,
EI) m/z (%) 335 [M , 58], 318 (77), 308 (27), 292 (99), 223 (78),
1
26.0, 127.8, 135.4, 135.5, 141.1, 152.8, 159.3, 177.4; MS (70
1
3
4
3
35 (100); HRMS calcd for C17
35.0588. Anal. Calcd for C17
.18. Found: C, 60.87; H, 3.64; N, 4.16. IR (CHCl
536, 1460, 1365, 1323, 1168, 1130, 1069, 1016, 844.
-(1,3-Benzothiazol-2-yl)-1-(4-nitrophenyl)-2-propen-1-
ol (26b): yellow oil; R 0.11 (8:2 petroleum ether:diethyl ether);
H NMR (300 MHz, CDCl ) δ 4.35 (s, 1H, OH), 5.48 (d, 1H, J
10.5 Hz), 5.52 (d, 1H, J ) 17.0 Hz), 6.71 (dd, 1H, J ) 17.0
Hz, J ) 10.5 Hz), 7.35-7.60 (m, 2H), 7.80 (d, 2H, J ) 8.5 Hz),
.72-7.95 (m, 1H), 7.90-8.10 (m, 1H), 8.18 (d, 2H, J ) 8.5
H
12 3
12
F
3
NOS 335.0592, found
+
eV, EI) m/z (%) 297 [M , 11], 279 (4), 162 (21), 135 (100), 108
(16); HRMS calcd for C17 S 297.0824, found 297.0821.
Anal. Calcd for C17 S: C, 68.66; H, 5.08; N, 4.71.
Found: C, 68.64; H, 5.10; N, 4.68. IR (CHCl
H F NOS: C, 60.89; H, 3.61; N,
-
1
H
15NO
2
2
3
) (ν, cm )
H
15NO
-
1
3
) (ν, cm ) 3693,
586, 3471, 1607, 1511, 1435, 1301, 1252, 1175, 1038, 988, 896,
32.
,3-Benzothiazol-2-yl[4-(trifluoromethyl)phenyl]-
methyl vinyl ether (27a): colorless oil, R 0.45 (8:2 petroleum
ether:diethyl ether); H NMR (300 MHz, CDCl ) δ 4.26 (dd,
1
3
8
f
1
3
1
)
f
1
3
7
1
2
7
H, J ) 6.8 Hz, J ) 2.5 Hz), 4.52 (dd, 1H, J ) 14.3 Hz, J )
1
3
3
Hz); C NMR (75.46 MHz, CDCl ) δ 78.6, 116.8, 121.7, 123.3,
.5 Hz), 6.36 (s, 1H), 6.56 (dd, 1H, J ) 14.3 Hz, J ) 6.8 Hz),
.39 (td, 1H, J ) 8.0 Hz, J ) 1.3 Hz), 7.49 (td, 1H, J ) 7.3 Hz,
1
1
2
C
C
3
1
25.1, 125.6, 126.4, 127.1, 135.2, 140.2, 147.4, 149.9, 152.6,
+
75.4; MS (70 eV, EI) m/z (%) 312 [M , 97], 295 (80), 283 (21),
J ) 1.3 Hz), 7.65 (d, 2H, J ) 8.2 Hz), 7.72 (d, 2H, J ) 8.2 Hz),
69 (34), 223 (48), 162 (49), 135 (100); HRMS calcd for
7
.88 (dd, 1H, J ) 8.2 Hz, J ) 1.9 Hz), 8.03 (dd, 1H, J ) 8.2
16
H
H
12
N
2
O
3
S 312.0569, found 312.0571. Anal. Calcd for
13
Hz, J ) 0.6 Hz); C NMR (75.46 MHz, CDCl
3
) δ 79.5, 91.8,
), 125.5, 125.7 (q, J )
), 126.2, 126.9, 130.7 (q, J ) 32.6 Hz,
3
), 134.9, 141.9, 149.3, 152.6, 171.4; MS (70 eV, EI) m/z
16
12 2 3
N O S: C, 61.53; H, 3.87; N, 8.97. Found: C, 61.51; H,
1
21.8, 123.3, 123.8 (q, J ) 272.3 Hz, CF
.6 Hz, CH-C-CF
3
-
1
.89; N, 9.00. IR (CHCl
351, 1259, 1099, 1015, 938, 854.
-(1,3-Benzothiazol-2-yl)-1-(4-chlorophenyl)-2-propen-
-ol (26c): white solid, mp 115-117 °C (from CH OH); R 0.30
3
) (ν, cm ) 3594, 3364, 1603, 1523,
3
3
C-CF
1
(%) 335 [M , 8], 292 (100), 223 (78); HRMS calcd for C H F -
+
17 12 3
1
3
f
NOS 335.0592, found 335.0589. IR (CHCl ) (ν, cm-1) 3536,
3
1
(
8:2 petroleum ether:diethyl ether); H NMR (300 MHz, CDCl
3
)
1639, 1620, 1324, 1171, 1133, 1069, 1016, 959, 845.
δ 4.00 (br s, 1H, OH), 5.45 (d, 1H, J ) 10.5 Hz), 5.51 (d, 1H,
J ) 17.1 Hz), 6.67 (dd, 1H, J ) 17.1 Hz, J ) 10.5 Hz), 7.30-
1
,3-Benzothiazol-2-yl(4-nitrophenyl)methyl vinyl ether
27b): pale yellow oil; R 0.24 (8:2 petroleum ether:diethyl
ether); H NMR (400 MHz, CDCl ) δ 4.28 (dd, 1H, J ) 6.7 Hz,
(
f
7
1
7
1
.60 (m, 6H), 7.87 (dd, 1H, J ) 7.3 Hz, J ) 0.7 Hz), 8.02 (dd,
1
3
H, J ) 8.1 Hz, J ) 0.7 Hz); 13C NMR (75.46 MHz, CDCl
3
) δ
J ) 2.8 Hz), 4.51 (dd, 1H, J ) 14.2 Hz, J ) 2.8 Hz), 6.36 (s,
8.7, 116.1, 121.7, 123.2, 125.3, 126.2, 128.0, 128.5, 134.1,
1
H), 6.58 (dd, 1H, J ) 14.2 Hz, J ) 6.7 Hz), 7.36-7.52 (m,
H), 7.76 (d, 2H, J ) 8.5 Hz), 7.85-7.90 (m, 1H), 7.98-8.03
35.4, 140.7, 141.7, 152.7, 176.5; MS (70 eV, EI) m/z (%) 301
2
(
+
[
(
M , 24], 284 (10), 246 (10), 162 (30), 139 (30), 135 (73), 111
13
m, 1H), 8.24 (d, 2H, J ) 8.5 Hz); C NMR (100.56 MHz,
37), 55 (100); HRMS calcd for C16
H
12ClNOS 301.0328, found
CDCl
3
) δ 79.2, 92.1, 121.9, 123.4, 124.0, 125.6, 126.4, 127.5,
3
4
3
01.0332. Anal. Calcd for C16
.64. Found: C, 63.65; H, 4.03; N, 4.67. IR (CHCl
678, 3594, 3425, 1591, 1488, 1094, 1015, 942, 893, 820.
-(1,3-Benzothiazol-2-yl)-1-(4-fluorophenyl)-2-propen-
-ol (26d): white solid, mp 148-150 °C (from CH OH); R 0.21
H12ClNOS: C, 63.68; H, 4.01; N,
1
35.0, 144.9, 147.9, 149.3, 152.8, 170.4; MS (70 eV, EI) m/z
-
1
) (ν, cm
)
+
3
(
%) 312 [M , 9], 284 (12), 269 (57), 223 (100); HRMS calcd for
-1
C
16 12 2 3 3
H N O S 312.0569, found 312.0571. IR (CHCl ) (ν, cm )
1
3620, 1525, 1346, 1223, 1187, 1046, 928, 852.
1
3
f
1,3-Benzothiazol-2-yl(4-chlorophenyl)methylvinylether
1
(
8:2 petroleum ether:diethyl ether); H NMR (300 MHz, CDCl
3
)
(27c): colorless oil; R 0.50 (8:2 petroleum ether:diethyl ether);
f
1
δ 3.99 (br s, 1H, OH), 5.44 (d, 1H, J ) 10.5 Hz), 5.51 (d, 1H,
J ) 17.1 Hz), 6.67 (dd, 1H, J ) 17.1 Hz, J ) 10.5 Hz), 6.98-
7
8
)
Hz), 139.4 (d, J ) 60 Hz), 141.0, 152.8, 160.9, 164.1, 176.5;
MS (70 eV, EI) m/z (%) 285 [M , 27], 268 (51), 257 (22), 190
H NMR (300 MHz, CDCl ) δ 4.23 (dd, 1H, J ) 6.8 Hz, J )
3
2.5 Hz), 4.50 (dd, 1H, J ) 14.2 Hz, J ) 2.5 Hz), 6.26 (s, 1H),
6.55 (dd, 1H, J ) 14.2 Hz, J ) 6.8 Hz), 7.36 (d, 2H, J ) 8.4
Hz), 7.33-7.42 (m, 1H), 7.42-7.55 (m, 1H), 7.51 (d, 2H, J )
.10 (m, 2H), 7.30-7.60 (m, 4H), 7.83-7.90 (m, 1H), 7.98-
13
3
.06 (m, 1H); C NMR (75.46 MHz, CDCl ) δ 78.7, 115.3 (d, J
1
3
21.6 Hz), 115.9, 121.8, 123.3, 125.3, 126.2, 128.5 (d, J ) 8.1
8.4 Hz), 7.87 (d, 1H, J ) 8.0 Hz), 8.01 (d, 1H, J ) 8.2 Hz);
C
3
NMR (75.46 MHz, CDCl ) δ 79.6, 91.6, 121.8, 123.3, 125.4,
+
126.1, 128.0, 128.9, 134.5, 135.0, 136.6, 149.4, 152.7, 171.7;
+
(6), 151 (18), 135 (100), 95 (54); HRMS calcd for C16
2
H
12FNOS
MS (70 eV, EI) m/z (%) 301 [M , 6], 258 (65), 223 (100), 139
85.0624, found 285.0621. Anal. Calcd for C16
H
12FNOS: C,
(6), 111 (23); HRMS calcd for C16H12ClNOS 301.0328, found
8908 J. Org. Chem., Vol. 69, No. 25, 2004