The Journal of Organic Chemistry
MHz, CDCl3) δ (ppm) 8.10−8.08 (m, 2H), 8.00 (d, J = 8.7 Hz,
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CDCl3) δ (ppm) 8.20−8.18 (m, 2H), 8.12 (d, J = 8.2 Hz, 1H),
7.95 (d, J = 8.1 Hz, 1H), 7.78 (d, J = 8.4 Hz, 2H), 7.58−7.54
(m, 1H), 7.49−7.45 (m, 1H). 13C{1H} NMR (100 MHz, CDCl3)
δ (ppm) 165.3, 153.9, 137.4, 135.3, 132.8, 127.9, 126.9,
126.1, 123.8, 121.8, 118.3, 114.1.
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1H), 7.89 (d, J = 2.0 Hz, 1H), 7.54−7.51 (m, 3H), 7.47 (dd, J =
8.7, 2.1 Hz, 1H). 13C{1H} NMR (100 MHz, CDCl3) δ (ppm)
168.6, 152.6, 136.2, 133.1, 131.3, 131.1, 129.1, 127.6,
127.2, 123.9, 121.3.
5-Chloro-2-phenylbenzo[d]thiazole (3n).12 White soild
2-(4-Nitrophenyl)benzo[d]thiazole (4e).19c White solid
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(34.3 mg, 70% yield). mp 137−139 C. H NMR (400 MHz,
CDCl3) δ (ppm) 8.14−8.04 (m, 3H), 7.81 (d, J = 8.5 Hz, 1H),
7.51−7.50 (m, 3H), 7.37−7.35 (m, 1H). 13C{1H} NMR (100
MHz, CDCl3) δ (ppm) 169.4, 154.5, 132.8, 132.8, 131.8,
130.8, 128.6, 127.1, 125.1, 122.6, 121.8.
(21.0 mg, 41% yield). mp 220−222 C. H NMR (400 MHz,
CDCl3) δ (ppm) 8.39−8.37 (m, 2H), 8.31−8.28 (m, 2H),
8.17−8.15 (m, 1H), 8.00−7.97 (m, 1H), 7.61−7.56 (m, 1H),
7.52−7.47 (m, 1H). 13C{1H} NMR (100 MHz, CDCl3) δ (ppm)
164.9, 154.1, 149.0, 139.2, 135.5, 128.2, 127.0, 126.3, 124.3,
123.9, 121.9.
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6-Bromo-2-phenylbenzo[d]thiazole (3o).7f White soild
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(40.5 mg, 70% yield). mp 154−156 C. H NMR (400 MHz,
CDCl3) δ (ppm) 8.11−8.08 (m, 2H), 8.00 (d, J = 8.7 Hz, 1H),
7.89 (d, J = 2.1 Hz, 1H), 7.56−7.50 (m, 3H), 7.48-7.46 (m,
1H). 13C{1H} NMR (100 MHz, CDCl3) δ (ppm) 168.6, 152.6,
136.2, 133.2, 131.3, 129.1, 127.5, 127.2, 123.9, 121.3,
121.2.
2-(4-(Trifluoromethyl)phenyl)benzo[d]thiazole
(4f).19b White soild (33.6 mg, 71% yield). mp 162−164 C.
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1H NMR (400 MHz, CDCl3) δ (ppm) 8.23 (d, J = 8.1 Hz, 2H),
8.14 (d, J = 8.2 Hz, 1H), 7.95 (d, J = 8.1 Hz, 1H), 7.78 (d, J =
8.2 Hz, 2H), 7.58−7.54 (m, 1H), 7.48−7.44 (m, 1H).13C{1H}
NMR (100 MHz, CDCl3) δ (ppm) 166.1, 153.9, 136.8, 135.2,
132.5 (q, J = 32.6 Hz), 127.8, 126.7, 126.0 (q, J = 3.7 Hz),
125.8, 123.6 (q, J = 273.4 Hz), 122.5, 121.8.
5-Bromo-2-phenylbenzo[d]thiazole (3p).12 White soild
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(39.9 mg, 69% yield). mp 134−136 C. H NMR (400 MHz,
CDCl3) δ (ppm) 8.23 (s, 1H), 8.09−8.07 (m, 2H), 7.75 (d, J =
8.5 Hz, 1H), 7.51−7.48 (m, 4H). 13C{1H} NMR (100 MHz,
CDCl3) δ (ppm) 169.6, 155.2, 133.8, 133.1, 131.2, 129.0,
128.1, 127.5, 126.0, 122.5, 119.8.
2-(4-Fluorophenyl)benzo[d]thiazole (4g).19b White
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solid (32.5 mg, 71% yield). mp 99−101 C. H NMR (400
MHz, CDCl3) δ (ppm) 8.13−8.08 (m, 3H), 7.92 (d, J = 8.4 Hz,
1H), 7.52 (ddd, J = 8.3, 7.2, 1.3 Hz, 1H), 7.42 (ddd, J = 8.2,
7.2, 1.2 Hz, 1H), 7.24−7.18 (m, 2H). 13C{1H} NMR (100 MHz,
CDCl3) δ (ppm) 166.8, 164.5 (d, J = 252.0 Hz), 154.0, 135.0,
129.9 (d, J = 3.2 Hz), 129.6 (d, J = 8.7 Hz), 126.5, 125.3,
123.2, 121.7, 116.2 (d, J = 22.1 Hz).
5,7-Dimethyl-2-phenylbenzo[d]thiazole (3q).11 Light
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yellow solid (32.5 mg, 68% yield). mp 87−89 C. H NMR
(400 MHz, CDCl3) δ (ppm) 8.14−8.12 (m, 2H), 7.76 (s, 1H),
7.51 (dd, J = 5.1, 1.8 Hz, 3H), 7.05 (s, 1H), 2.58 (s, 3H), 2.51
(s, 3H). 13C{1H} NMR (100 MHz, CDCl3) δ (ppm) 167.6,
154.3, 136.6, 133.9, 132.5, 131.1, 130.8, 129.0, 127.5,
127.1, 120.7, 21.5, 21.3.
2-(4-Chlorophenyl)benzo[d]thiazole (4h).7f White solid
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(37.7 mg, 77% yield). mp 114−116 C. H NMR (400 MHz,
CDCl3) δ (ppm) 8.10 (d, J = 8.2 Hz, 1H), 8.07−8.02 (m, 2H),
7.92 (d, J = 7.7 Hz, 1H), 7.55−7.51 (m, 1H), 7.50−7.47 (m,
2H), 7.44−7.40 (m, 1H). 13C{1H} NMR (100 MHz, CDCl3) δ
(ppm) 166.6, 154.0, 137.1, 135.0, 132.0, 129.3, 128.7,
126.5, 125.4, 123.3, 121.7.
2-Phenylnaphtho[2,1-d]thiazole (3r).11 White soild
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(39.7 mg, 76% yield). mp 100−102 C. 1H NMR (400 MHz,
CDCl3) δ (ppm) 8.20−8.14 (m, 3H), 8.07 (d, J = 8.2 Hz, 1H),
8.00 (d, J = 8.1 Hz, 1H), 7.92 (d, J = 8.8 Hz, 1H), 7.66−7.58
(m, 2H), 7.55−7.52 (m, 3H). 13C{1H} NMR (100 MHz, CDCl3)
δ (ppm) 167.3, 152.0, 133.6, 132.1, 131.1, 130.8, 129.1,
129.0, 128.1, 127.5, 127.4, 127.1, 126.1, 125.2, 121.7.
2-(p-Tolyl)benzo[d]thiazole (4a).7f White soild (32.9
2-(3-Chlorophenyl)benzo[d]thiazole (4i).19c White solid
(30.9 mg, 63% yield). mp 95−97 oC. 1H NMR (400 MHz,
CDCl3) δ (ppm) 8.15−8.14 (m, 1H), 8.12 (d, J = 8.2 Hz, 1H),
7.99−7.96 (m, 1H), 7.94 (d, J = 8.0 Hz, 1H), 7.56−7.52 (m,
1H), 7.50−7.42 (m, 3H). 13C{1H} NMR (100 MHz, CDCl3) δ
(ppm) 166.3, 153.9, 135.2, 135.0, 130.9, 130.3, 127.4,
126.6, 126.5, 125.7, 125.6, 123.4, 121.7.
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mg, 73% yield). mp 86−88 oC. H NMR (400 MHz, CDCl3) δ
(ppm) 8.10 (d, J = 8.1 Hz, 1H), 8.02 (d, J = 8.2 Hz, 2H), 7.91
(d, J = 7.9 Hz, 1H), 7.53−7.49 (m, 1H), 7.42−7.38 (m, 1H),
7.32 (d, J = 8.0 Hz, 2H), 2.45 (s, 3H). 13C{1H} NMR (100
MHz, CDCl3) δ (ppm) 168.3, 154.1, 141.5, 134.9, 130.9,
129.7, 127.5, 126.3, 125.0, 123.0, 121.6, 21.5.
2-(2-Chlorophenyl)benzo[d]thiazole (4j).19b White
solid (31.9 mg, 65% yield). mp 84−86 oC. 1H NMR (400
MHz, CDCl3) δ (ppm) 8.27−8.17 (m, 1H), 8.18 (d, J = 8.1 Hz,
1H), 7.98 (d, J = 8.0 Hz, 1H), 7.58−7.54 (m, 2H), 7.48−7.43
(m, 3H). 13C{1H} NMR (100 MHz, CDCl3) δ (ppm) 164.2,
152.4, 136.1, 132.7, 132.2, 131.8, 131.2, 130.8, 127.2,
126.4, 125.5, 123.5, 121.4.
3-(2-Methylbenzo[4,5][1,3,6]thiadiazepino[3,2-
a]indol-6-yl)propan-1-ol (4b).7f White soild (36.2 mg,
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75% yield). mp 119−121 C. H NMR (400 MHz, CDCl3) δ
(ppm) 8.08−8.05 (m, 3H), 7.89 (d, J = 7.9 Hz, 1H),
7.52−7.48 (m, 1H), 7.40−7.36 (m, 1H), 7.04−7.00 (m, 2H),
3.90 (s, 3H). 13C{1H} NMR (100 MHz, CDCl3) δ (ppm) 167.9,
162.0, 154.1, 134.8, 129.1, 126.4, 126.2, 124.8, 122.8,
121.5, 114.4, 55.5.
2-(4-Bromophenyl)benzo[d]thiazole (4k).19c White
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solid (39.9 mg, 69% yield). mp 130−132 C. H NMR (400
MHz, CDCl3) δ (ppm) 8.09 (d, J = 8.1 Hz, 1H), 7.98 (d, J = 8.6
Hz, 2H), 7.92 (dd, J = 8.1, 1.5 Hz, 1H), 7.66−7.63 (m, 2H),
7.55−7.51 (m, 1H), 7.44−7.40 (m, 1H). 13C{1H} NMR (100
MHz, CDCl3) δ (ppm) 166.7, 154.0, 135.0, 132.5, 132.2,
128.9, 126.5, 125.5, 125.5, 123.3, 121.7.
4-(Benzo[d]thiazol-2-yl)-N,N-dimethylaniline (4c).7g
Yellow soild (35.6 mg, 70% yield). mp 169−171 oC. 1H NMR
(400 MHz, CDCl3) δ (ppm) 8.03−7.97 (m, 3H), 7.86 (d, J =
7.8 Hz, 1H), 7.48−7.44 (m, 1H), 7.35−7.31 (m, 1H),
6.78−6.75 (m, 2H), 3.07 (s, 6H). 13C{1H} NMR (100 MHz,
CDCl3) δ (ppm) 168.9, 154.3, 152.2, 134.5, 128.9, 126.0,
124.2, 122.2, 121.4, 121.3, 111.7, 40.2.
2-(3,5-Dimethoxyphenyl)benzo[d]thiazole
(4l).19b
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White solid (35.8 mg, 66% yield). mp 85−87 C. H NMR
(400 MHz, CDCl3) δ (ppm) 8.11 (d, J = 8.1 Hz, 1H), 7.92 (d, J
= 7.6 Hz, 1H), 7.54−7.50 (m, 1H), 7.44−7.39 (m, 1H), 7.29
(d, J = 2.3 Hz, 2H), 6.62 (t, J = 2.3 Hz, 1H), 3.92 (s, 6H).
13C{1H} NMR (100 MHz, CDCl3) δ (ppm) 168.0, 161.1,
4-(Benzo[d]thiazol-2-yl)benzonitrile (4d).7f White solid
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(32.1 mg, 68% yield). mp 168−170 C. H NMR (400 MHz,
ACS Paragon Plus Environment