Green Chemistry
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(
100 MHz, DMSO-d
6
) δ 167.6, 153.7, 149.0, 145.8, 134.1, 126.3, 7.59 (d, 2H, Ar, J = 7.2 Hz), 7.28–7.22 (m, 3H, Ar), 7.21–7.19 (m,
1
3
1
24.8, 124.4, 122.2, 122.0, 119.4, 116.1, 114.0. Anal. Calcd for 2H, Ar), 6.84 (d, 1H, Ar, J = 7.5 Hz); C NMR (100 MHz,
NO S: C, 64.18; H, 3.73; N, 5.76. Found: C, 63.98; H, DMSO-d ) δ 157.8, 149.8, 137.7, 137.5, 132.2, 130.7, 123.6,
.84; N, 5.77.
-(Benzo[d]thiazol-2-yl)benzene-1,2-diol
400 MHz, DMSO-d
.55 (t, 2H, Ar, J = 8.72 Hz), 7.28–7.38 (m, 2H, Ar), 7.16 (d, 1H,
Ar, J = 7.8 Hz), 6.99 (d, 1H, Ar, J = 7.36 Hz), 6.84 (t, 1H, Ar, J = (400 MHz, DMSO-d ) δ 12.92 (s, 2H, NH, OH), 7.59–7.56 (m,
C
3
13
H
9
2
6
123.3, 119.1, 118.49, 117.1, 115.1, 114.4. Anal. Calcd for
1
3
(19).
H
NMR C H N O: C, 74.27; H, 4.79; N, 13.33. Found: C, 74.21; H,
1
3
10 2
(
7
6
) δ 9.33 (s, 1H, –OH), 9.02 (s, 1H, –OH), 4.68; N, 13.49.
2-(1H-Benzo[d]imidazol-2-yl)phenol
1
(27).
H
NMR
6
1
3
7
1
1
.8 Hz); C NMR (100 MHz, DMSO-d
6
) δ 164.1, 149.0, 145.8, 2H, Ar), 7.43 (d, 1H, Ar, J = 7.4 Hz), 7.27–7.24 (m, 2H, Ar), 7.19
45.6, 130.1, 128.1, 127.9, 126.3, 123.0, 119.6, 119.5, 119.1, (t, 1H, Ar, J = 7.5 Hz), 7.00 (t, 1H, Ar, J = 7.5 Hz), 6.92 (d, 1H,
18.4. Anal. Calcd for C H NO S: C, 64.18; H, 3.73; N, 5.76. Ar, J = 7.5 Hz); C NMR (100 MHz, DMSO-d ) δ 158.6, 152.0,
1
3
1
3
9
2
6
Found: C, 64.29; H, 3.72; N, 6.01.
-(Benzo[d]thiazol-2-yl)-5-(diethylamino)phenol
NMR (400 MHz, CDCl ) δ 13.29 (s, 1H, –OH), 8.45 (s, 1H, Ar), 13.33. Found: C, 74.32; H, 4.81; N, 13.43.
137.7, 137.5, 131.0, 129.9, 123.6, 123.3, 121.1, 118.5, 118.4,
115.1, 111.4. Anal. Calcd for C13H N O: C, 74.27; H, 4.79; N,
10 2
1
2
(20).
H
3
1
7
.62 (d, 1H, Ar, J = 7.76 Hz), 7.21–7.08 (m, 3H, Ar), 6.24–6.29
m, 2H, Ar), 3.42 (q, 4H, 2CH , J = 7.08 Hz), 1.22 (t, 6H, 2CH
J = 7.04 Hz); C NMR (100 MHz, CDCl ) δ 163.6, 160.9, 152.1, 2H, Ar), 2.50 (s, 3H, CH3); C NMR (100 MHz, CDCl ) δ 155.2,
2-Methyl-1H-benzo[d]imidazole (28). H NMR (400 MHz,
(
2
3
,
CDCl ) δ 9.19 (s, 1H, NH), 7.55–7.52 (m, 2H, Ar), 7.25–7.19 (m,
3
1
3
13
3
3
1
9
46.9, 134.2, 131.3, 127.1, 126.4, 126.2, 117.2, 109.2, 104.0, 138.7, 138.4, 121.6, 120.7, 117.8, 114.1, 13.7. Anal. Calcd for
7.8, 44.8, 12.8. Anal. Calcd for C17
H
18
N
2
OS: C, 68.42; H, 6.08;
C
8
H
8
N
2
: C, 72.70; H, 6.10; N, 21.20. Found: C, 72.89; H, 5.97;
N, 21.49.
6
Benzo[d]oxazole (29). H NMR (400 MHz, DMSO-d ) δ 7.95
N, 9.39. Found: C, 68.82; H, 6.15; N, 9.14.
-(Benzo[d]thiazol-2-yl)-4-nitrophenol
400 MHz, DMSO-d
1
1
3
(21).
H
NMR
1
3
(
6
) δ 11.09 (s, 1H, –OH), 8.09 (d, 1H, Ar, J = (s, 1H, Ar), 7.33–7.27 (m, 4H, Ar); C NMR (100 MHz, DMSO-
.92 Hz), 7.14 (s, 1H, Ar), 6.98–6.84 (m, 3H, Ar), 6.74–6.77 (m, d6) δ 155.3, 151.2, 139.9, 124.6, 123.9, 117.5, 110.1. Anal. Calcd
8
1
1
3
H, Ar), 6.62 (t, 1H, Ar, J = 7.44 Hz); C NMR (100 MHz, for C
) δ 163.3, 147.5, 143.9, 136.6, 129.8, 128.7, 125.5, 4.15; N, 11.83.
24.5, 121.3, 119.3, 115.0, 113.7, 109.4. Anal. Calcd for 2-Phenylbenzo[d]oxazole (30). H NMR (400 MHz, DMSO-d6)
S: C, 57.35; H, 2.96; N, 10.29. Found: C, 57.45; H, δ 8.24 (dd, 2H, Ar, J = 7.4, 1.4 Hz), 7.83 (t, 2H, Ar, J = 7.4 Hz),
7 5
H NO: C, 70.58; H, 4.23; N, 11.76. Found: C, 70.63; H,
DMSO-d
1
C H N O
13 8 2 3
6
1
1
3
2
.98; N, 10.25.
2
6
7.39–7.29 (m, 5H, Ar); C NMR (100 MHz, DMSO-d ) δ 160.9,
1
-Methylbenzo[d]thiazole (22). H NMR (400 MHz, CDCl ) δ 152.1, 138.3, 132.0, 129.4, 129.2, 127.9, 125.5, 124.4, 118.3,
3
2
.82 (s, 3H, CH
3
), 7.34–7.32 (m, 2H, Ar), 7.94 (d, 1H, Ar, J = 8.0 111.2. Anal. Calcd for C13
H
19NO: C, 79.98; H, 4.65; N, 7.17.
) δ Found: C, 80.02; H, 4.71; N, 7.25.
66.8, 152.3, 136.30, 127.3, 123.3, 123.3, 121.8, 19.0. Anal. 4-(Benzo[d]oxazol-2-yl)phenol (31).
NS: C, 64.39; H, 4.73; N, 9.39. Found: C, 64.42; CDCl ) δ 8.53 (s, 1H, OH), 7.76 (d, 2H, Ar, J = 8.5 Hz), 7.69 (d,
1H, Ar, J = 8.5 Hz), 7.09 (t, 1H, Ar, J = 7.7 Hz), 6.94–6.89 (m,
1
3
Hz), 8.0 (d, 1H, Ar, J = 8.1 Hz); C NMR (100 MHz, CDCl
1
Calcd for C
H, 4.79; N, 9.35.
H-Benzo[d]imidazole (23). H NMR (400 MHz, DMSO-d ) δ 3H, Ar), 6.83 (t, 1H, Ar, J = 8.3 Hz); C NMR (100 MHz, CDCl3)
3
1
H NMR (400 MHz,
8
H
7
3
1
13
1
6
1
7
1
2.73 (br, s, 1H, NH), 8.05 (s, 1H, Ar), 7.84–7.78 (m, 2H, Ar), δ 159.3, 156.8, 152.1, 132.5, 130.9, 128.4, 121.5, 120.2, 119.7,
1
3
.24–7.21 (m, 2H, Ar); C NMR (100 MHz, DMSO-d
6 9 2
) δ 144.3, 116.0, 114.83. Anal. Calcd for C13H NO : C, 73.92; H, 4.29; N,
39.3, 137.1, 122.45, 121.7, 117.9, 114.0. Anal. Calcd for 6.63. Found: C, 74.03; H, 4.21; N, 6.69.
1
C
7
H
6
N
2
: C, 71.17; H, 5.12; N, 23.71. Found: C, 71.10; H, 5.14;
3-(Benzo[d]oxazol-2-yl)phenol (32).
CDCl ) δ 8.62 (s, 1H, OH), 7.45 (s, 1H, Ar), 7.39–7.27 (m, 3H,
-Phenyl-1H-benzo[d]imidazole (24). H NMR (400 MHz, Ar), 7.19 (t, 1H, Ar, J = 7.7 Hz), 6.99 (t, 2H, Ar, J = 7.7 Hz), 6.90
H NMR (400 MHz,
N, 23.69.
3
1
2
1
3
6 3
DMSO-d ) δ 12.88 (s, 1H, NH), 8.13 (d, 2H, Ar, J = 7.8 Hz), 7.62 (t, 1H, Ar, J = 7.6 Hz); C NMR (100 MHz, CDCl ) δ 157.1,
(
7
d, 1H, Ar, J = 7.6 Hz), 7.53–7.47 (m, 4H, Ar), 7.16 (t, 2H, Ar, J = 156.3, 152.2, 137.43, 130.2, 129.1, 123.6, 122.3, 120.4, 119.2,
.8 Hz); C NMR (100 MHz, DMSO-d ) δ 151.7, 144.3, 135.5, 116.1, 115.14, 114.2. Anal. Calcd for C H NO : C, 73.92; H,
6 13 9 2
1
3
1
30.6, 130.4, 129.5, 126.9, 123.1, 122.2, 119.4, 111.9. Anal. 4.29; N, 6.63. Found: C, 73.95; H, 4.27; N, 6.60.
1
Calcd for C13
0.42; H, 5.17; N, 14.45.
-(1H-Benzo[d]imidazol-2-yl)phenol
400 MHz, DMSO-d
H
10
N
2
: C, 80.39; H, 5.19; N, 14.42. Found: C,
2-(Benzo[d]oxazol-2-yl)phenol (33). H NMR (400 MHz,
8
CDCl ) δ 8.68 (s, 1H, OH), 7.41 (t, 2H, Ar, J = 8.0 Hz), 7.23–7.17
3
1
4
(25).
H
NMR (m, 1H, Ar), 7.14 (dd, 1H, Ar, J = 7.9, 1.4 Hz), 7.04–6.96 (m, 4H,
1
3
(
6
) δ 12.66 (s, 1H, NH), 9.92 (s, 1H, OH), Ar); C NMR (100 MHz, CDCl
3
) δ 159.0, 152.1, 151.77, 138.,
7
2
.59–7.56 (m, 2H, Ar), 7.47 (d, 2H, Ar, J = 7.5 Hz), 7.28–7.24 (m, 132.9, 130.5, 125.5, 124.4, 120.0, 118.3, 117.6, 113.3, 111.2.
1
3
H, Ar), 6.92 (d, 2H, Ar, J = 7.5 Hz); C NMR (100 MHz, Anal. Calcd for C13
H
9
NO
2
: C, 73.92; H, 4.29; N, 6.63. Found: C,
DMSO-d
21.0, 118.5, 116.2, 115.1. Anal. Calcd for C H N O: C, 74.27;
6
) δ 160.7, 150.3, 137.7, 137.5, 127.0, 123.6, 123.3, 73.89; H, 4.26; N, 6.59.
1
1
2-Methylbenzo[d]oxazole (34). H NMR (400 MHz, CDCl ) δ
1
3
10
2
3
H, 4.79; N, 13.33. Found: C, 74.69; H, 4.61; N, 12.99.
7.68–7.64 (m, 1H, Ar), 7.42–7.41 (m, 1H, Ar), 7.30–7.25 (m, 2H,
NMR Ar), 2.54 (s, 3H, CH ); C NMR (100 MHz, CDCl ) δ 166.8,
3 3
1
13
3
-(1H-Benzo[d]imidazol-2-yl)phenol
(26).
H
(
400 MHz, DMSO-d ) δ 12.27 (s, 1H, NH), 10.52 (s, 1H, OH), 151.6, 141.8, 123.7, 123.4, 117.7, 111.6, 14.8. Anal. Calcd for
6
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Green Chem.