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7.30 (dd, 1H, J = 7.6, 1.4 Hz), 7.24–7.07 (m, 2H), 6.71–
6.61 (m, 2H), 6.26 (d, 1H, J = 11.0 Hz), 6.06 (d, 1H,
J = 10.6 Hz), 4.39 (br s, 2H); 13C NMR (CDCl3,
50 MHz) d 149.9, 148.7, 142.9, 136.0, 131.8, 130.3,
127.5, 122.8, 121.5, 117.3, 116.7, 114.0, 106.8, 95.7,
95.6, 93.0, 87.4; MS (EI) [m/z (relative intensity)] 244
(M+, 100), 243 (91), 241 (24); HRMS calcd for
C17H12N2, Mr = 244.1001, found 244.0995.
5.22. (1-(2-Anilinylethynyl)-2-(2-pyridinylethynyl))-
benzene (18)
1H NMR (CDCl3, 200 MHz) d 8.60 (dd, 1H, J = 4.0,
0.8 Hz), 7.67–7.52 (m, 4H), 7.43–7.07 (m, 5H), 6.71–
6.64 (m, 2H), 4.41 (br s, 2H); 13C NMR (CDCl3,
50 MHz) d 149.8, 148.4, 143.2, 135.9, 132.4, 131.9,
131.3, 129.8, 128.6, 127.5, 127.5, 126.3, 123.9, 122.7,
117.3, 114.1, 107.3, 93.3, 92.2, 91.0, 88.4; MS (EI) [m/z
(relative intensity)] 249 (M+, 100), 291 (35); HRMS
calcd for C21H14N2, Mr = 294.1157, found 294.1127.
5.18. 2-(6-(2-Anisolyl)-3(Z)-hexen-1,5-diynyl)aniline (14)
1H NMR (CDCl3, 200 MHz) d 7.47 (dd, 1H, J = 7.4,
1.6 Hz), 7.36–7.28 (m, 2H), 7.13 (td, 1H, J = 7.4,
1.6 Hz), 6.96 (d, 1H, J = 8.0 Hz), 6.89 (d,
1H, J = 8.0 Hz), 6.72–6.64 (m, 2H), 6.15 (m, 2H), 4.41
(br s, 2H), 3.85 (s,3H); 13C NMR (CDCl3, 50 MHz) d
159.9, 148.3, 133.8, 130.1, 130.0, 120.4, 119.0, 118.4,
117.4, 114.0, 112.2, 110.8, 107.4, 94.3, 93.6, 93.2, 91.7,
55.6; MS (EI) [m/z (relative intensity)] 273 (M+, 85),
272 (52), 257 (100), 254 (25), 231 (36), 168 (40); HRMS
calcd for C19H15ON, Mr = 273.1154, found 273.1126.
5.23. (1-(2-Anilinylethynyl)-2-(2-anisolylethynyl))benzene
(19)
1H NMR (CDCl3, 200 MHz) d 7.56–7.52 (m, 3H), 7.41
(dd, 1H, J = 7.8, 1.6 Hz), 7.38–7.28 (m, 3H), 6.99–6.87
(m, 2H), 6.73–6.64 (m, 2H), 4.01 (br s, 2H), 3.83 (s,
3H); 13C NMR (CDCl3, 50 MHz) 160.1, 148.3, 133.8,
132.1, 132.0, 131.4, 130.0, 129.7, 127.9, 127.6, 125.8,
125.5, 120.4, 117.4, 113.9, 112.4, 110.8, 107.7, 93.7,
92.7, 90.4, 89.6, 55.8; MS (EI) [m/z (relative intensity)]
323 (M+, 100), 308 (23), 307 (31), 279 (28), 217 (21),
205 (20); HRMS calcd for C23H17ON, Mr = 323.1310,
found 323.1310.
5.19. 2-(6-(2-Pyrazinyl)-3(Z)-hexen-1,5-diynyl)aniline
(15)
1H NMR (CDCl3, 200 MHz) d 8.71 (d, 1H, J = 1.6 Hz),
8.55 (t, 1H, J = 2.6 Hz), 8.46 (d, 1H, J = 2.4 Hz), 7.30 (d,
1H, J = 2.0 Hz), 7.13 (td, 1H, J = 8.0, 1.4 Hz), 6.72–6.63
(m, 2H), 6.31 (d, 1H, J = 11.0 Hz), 6.07 (d, 1H,
J = 11.0 Hz), 4.21 (br s, 2H); 13C NMR (CDCl3,
50 MHz) d 148.7, 147.9, 144.5, 142.8, 140.0, 132.0,
130.6, 122.9, 117.6, 115.9, 114.2, 106.7, 96.5, 92.8,
92.7, 91.4; MS (EI) [m/z (relative intensity)] 245 (M+,
100), 244 (76), 192 (52), 191 (75), 190 (35), 164 (33);
HRMS calcd for C16H11N3, Mr = 245.0954, found
245.0964.
5.24. (1-(2-Anilinylethynyl)-2-(2-pyrazinylethynyl))-
benzene (20)
1H NMR (CDCl3, 200 MHz) d 8.79 (d, 1H, J = 1.4 Hz),
8.56 (dd, 1H, J = 2.6, 1.4 Hz), 8.47 (d, 1H, J = 2.6 Hz),
7.67–7.59 (m, 2H), 7.57–7.28 (m, 3H), 6.73–6.65 (m,
2H), 4.26 (br s, 2H); 13C NMR (CDCl3, 50 MHz) d
148.4, 148.1, 144.3, 142.8, 140.2, 132.6, 132.1, 131.6,
130.1, 129.3, 127.7, 126.6, 123.2, 117.6, 114.3, 107.3,
93.0, 92.5, 91.4, 89.4; MS (EI) [m/z (relative intensity)]
295 (M+, 61), 294 (35), 247 (11); HRMS calcd for
C20H13N3, Mr = 295.1109, found 295.1124.
5.20. 2-(6-(2-Thienyl)-3(Z)-hexen-1,5-diynyl)aniline (16)
5.25. (1-(2-Anilinylethynyl)-2-(2-thienylethynyl))benzene
(21)
1H NMR (CDCl3, 200 MHz) d 7.36 (dd, 1H, J = 5.4,
1.8 Hz), 7.33 (dd, 1H, J = 2.6, 1.2 Hz), 7.29 (dd, 1H,
J = 3.8, 1.2 Hz), 7.03 (dd, 1H, J = 5.2, 3.6 Hz), 6.74–
6.08 (m, 2H), 6.18 (d, 1H, J = 10.6 Hz), 6.09 (d, 1H,
J = 10.6 Hz), 4.35 (br s, 2H); 13C NMR (CDCl3,
50 MHz) d 148.3, 132.7, 131.9, 130.2, 128.0, 127.2,
122.9, 119.4, 117.6, 117.5, 114.1, 107.2, 94.9, 93.2,
91.8, 90.2; MS (EI) [m/z (relative intensity)] 249 (M+,
100), 247 (27), 246 (38), 208 (34); HRMS calcd for
C16H11NS, Mr = 249.0613, found 249.0594.
1H NMR (CDCl3, 200 MHz) d 7.60–7.53 (m, 2H), 7.44
(dd, 1H, J = 8.4, 1.8 Hz), 7.38–7.30 (m, 3H), 7.16 (td,
1H, J = 7.8, 1.6 Hz), 7.04 (dd, 1H, J = 4.6, 3.6 Hz),
6.75–6.68 (m, 2H), 4.12 (br s, 2H); 13C NMR (CDCl3,
50 MHz) d 148.1, 132.6, 131.9, 131.3, 129.9, 128.3,
127.7, 127.1, 125.6, 124.5, 122.8, 117.5, 114.0, 107.4,
93.5, 92.4, 90.6, 86.2; MS (EI) [m/z (relative intensity)]
299 (M+, 100), 298 (36), 297 (35), 265 (14), 216 (13),
214 (15), 149 (16); HRMS calcd for C20H13NS,
Mr = 299.0762, found 299.0777.
5.21. 2-(6-(2-Thieanisolyl)-3(Z)-hexen-1,5-diynyl)aniline
(17)
5.26. (1-(2-Anilinylethynyl)-2-(2-thieanisolylethynyl))-
benzene (22)
1H NMR (CDCl3, 200 MHz) d 7.45 (dd, 1H, J = 7.6,
1.4 Hz), 7.36–7.25 (m, 2H) 7.17–7.05 (m, 3H), 6.71–
6.63 (m, 2H), 6.17 (m, 2H), 2.42 (s, 3H); 13C NMR
(CDCl3, 50 MHz) d 148.2, 141.8, 132.7, 132.1, 130.0,
129.0, 124.3, 124.2, 121.1, 119.5, 117.8, 117.5, 114.0,
107.4, 94.6, 94.4, 93.8, 93.0, 15.0; MS (EI) [m/z (relative
intensity)] 289 (M+, 72), 274 (86), 273 (100), 272 (24);
HRMS calcd for C19H15NS, Mr = 289.0926, found
289.0921.
1H NMR (CDCl3, 200 MHz) d 7.69–7.51 (m, 3H), 7.45–
7.28 (m, 4H), 7.20–7.07 (m, 3H), 6.70–6.65 (m, 2H), 4.12
(br s, 2H), 2.44 (s, 3H); 13C NMR (CDCl3, 50 MHz) d
148.2, 142.1, 132.6, 132.3, 132.1, 131.5, 129.7, 128.9,
128.2, 127.6, 125.6, 125.1, 124.3, 124.2, 123.2, 117.5,
114.0, 107.8, 94.9, 93.6, 90.6, 90.5, 15.1; MS (EI) [m/z
(relative intensity)] 339 (M+, 55), 325 (25), 324 (87),