HETEROCYCLES, Vol. 71, No. 11, 2007
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mp 175-176 °C. 1H NMR (DMSO-d6) ꢀ 1.24 (m, 2H), 1.51 (m, 14H), 1.68 (m, 2H), 1.78 (m, 2H), 1.96 (m,
2H), 2.46 (m, 2H), 2.82 (m, 2H), 2.88 (m, 2H), 7.21 (m, 2H), 7.46 (m, 3H) 13C NMR (DMSO-d6) ꢀ 22.7,
22.8, 23.3, 23.8, 26.1, 26.7, 26.9, 27.3, 27.5, 27.7, 29.3, 32.9, 128.1, 128.3, 129.7, 130.3, 136.1, 138.4,
144.8, 146.6, 155.4, 157.2, 181.9, 208.3, 212.9. [M+1]=405. Anal. Calcd for C27H33NS: C, 80.35; H, 8.24;
N, 3.47. Found: C, 80.02; H, 8.53; N, 3.58.
4-Phenyl-2-thien-2-yl-5,6,7,8-tetrahydro[1]benzothieno[2,3-b]pyridine (15aa)
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mp 190 °C. H NMR (DMSO-d6) ꢀ 1.52 (m, 2H), 1.74 (m, 2H), 1.92 (m, 2H), 2.81 (m, 2H), 7.13 (t, J =
3.4 Hz, 1H), 7.42 (m, 2H), 7.48 (m, 3H), 7.63 (d, J = 4.4 Hz 1H), 7.68 (s, 1H), 7.87 (d, J = 2.7 Hz, 1H).
[M+1]=349. Anal. Calcd for C21H17NS2: C, 72.58; H, 4.93; N, 4.03. Found: C, 72.44; H, 4.76; N, 4.19.
2-(2-Furyl)-4-phenyl-5,6,7,8-tetrahydro[1]benzothieno[2,3-b]pyridine (15ab)
mp 199 °C. 1H NMR (DMSO-d6) ꢀ 1.52 (m, 2H), 1.74 (m, 2H), 1.94 (m, 2H), 2.82 (m, 2H), 6.65 (m, 1H),
7.22 (d, J = 3 Hz, 1H), 7.42 (m, 2H), 7.48 (m, 4H), 7.82 (s, 1H). [M+1]=332. Anal. Calcd for C21H17NOS:
C, 76.10; H, 5.17; N, 4.23. Found: C, 76.32; H, 5.05; N, 4.39.
4-Phenyl-2-(1H-pyrrol-2-yl)-5,6,7,8-tetrahydro[1]benzothieno[2,3-b]pyridine (15ac)
mp 215 °C. 1H NMR (DMSO-d6) ꢀ 1.51 (m, 2H), 1.73 (m, 2H), 1.91 (m, 2H), 2.79 (m, 2H), 6.14 (s, 1H),
6.89 (s, 2H), 7.40 (s, 2H), 7.49 (s, 3H), 11.75 (s, 1H). [M+1]=331. Anal. Calcd for C21H18N2S: C, 76.33;
H, 5.49; N, 8.48. Found: C, 76.21; H, 5.63; N, 8.37.
2-tert-Butyl-4-phenyl-5,6,7,8-tetrahydro[1]benzothieno[2,3-b]pyridine (15ad)
mp 120 °C. 1H NMR (DMSO-d6) ꢀ 1.35 (s, 9H), 1.51 (m, 2H), 1.74 (m, 2H), 1.93 (m, 2H), 2.87 (m, 2H),
7.12 (s, 1H), 7.36 (m, 2H), 7.44 (m, 3H). [M+1]=322. Anal. Calcd for C21H23NS: C, 78.46; H, 7.21; N,
4.36. Found: C, 78.37; H, 7.30; N, 4.29.
2-(1-Adamantyl)-4-phenyl-5,6,7,8-tetrahydro[1]benzothieno[2,3-b]pyridine (15ae)
mp 181 °C. 1H NMR (DMSO-d6) ꢀ 1.50 (m, 2H), 1.72 (m, 8H), 1.97 (m, 8H), 2.03 (m, 3H), 2.49 (m, 2H),
7.04 (s, 1H), 7.33 (m, 2H), 7.43 (m, 3H). [M+1]=401. Anal. Calcd for C27H29NS: C, 81.16; H, 7.32; N,
3.51. Found: C, 81.05; H, 7.77; N, 3.41.
3-(2-Chloroethyl)-2,4-diphenyl-5,6,7,8-tetrahydro[1]benzothieno[2,3-b]pyridine (15af)
Mp 146-147 °C. 1H NMR (DMSO-d6) ꢀ 1.48 (m, 2H), 1.71 (m, 4H), 2.79 (m, 2H), 2.88 (m, 2H), 3.22 (m,
2H), 7.41 (m, 2H), 7.52 (m, 8H). [M+1]=405. Anal. Calcd for C25H22ClNS: C, 74.33; H, 5.49; N, 3.47.
Found: C, 74.45; H, 5.65; N, 3.32.
Ethyl 3-methyl-4-phenyl-5,6,7,8-tetrahydro[1]benzothieno[2,3-b]pyridine-2-carboxylate (16aa)
mp 130 °C. 1H NMR (DMSO-d6) ꢀ 0.84 (t, J = 7.2 Hz, 3H), 1.47 (m, 2H), 1.80 (m, 4H), 2.54 (s, 3H), 2.80
13
(m, 2H), 3.92 (q, J = 7.2 Hz, 2H), 7.24 (m, 2H), 7.45 (m, 3H). C NMR (DMSO-d6) ꢀ 13.8, 22.4, 22.5,