Arkivoc 2019, ii, 0-0
Vieira, B. M. et al.
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3
(
s, 3H); C (CDCl3, 100 MHz): δ = 159.1, 151.2, 147.4, 134.0, 130.8, 128.8, 128.2, 128.1, 126.0, 125.5, 120.5,
117.4, 115.4, 112.7, 104.1, 55.2. MS: m/z (rel. int.) 380 (21.3), 273 (61.4), 194 (100.0), 78 (70.5).
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-Phenyl-3-(p-tolylselanyl)imidazo[1,2-a]pyridine (5f). White solid, mp 126.5-127.8 °C. Yield: 0.098 g (54%);
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NMR H (CDCl3, 400 MHz): δ =8.4 (d, J 6.9 Hz, 1H), 8.2 – 8.1 (m, 2H), 7.7 (dt, J 9.1, 1.1 Hz, 1H), 7.5 – 7.4 (m, 2H),
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7.4 – 7.3 (m, 2H), 7.1 – 7.0 (m, 4H), 6.8 (td, J 6.8, 1.1 Hz, 1H), 2.3 (s, 3H). NMR C (CDCl3, 100 MHz): δ = 151.5,
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47.6, 136.7, 133.8, 130.4, 128.8, 128.5, 128.4, 128.3, 126.9, 126.4, 125.6, 117.5, 112.9, 29.7, 20.9. MS: m/z
+
(
rel. int.) 364 (33.9), 284 (100), 193 (5.3), 78 (65.3). HRMS: Calcd. for C20H16N2Se [M+H] : 365.0552 found:
365.0551.
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-(Mesitylselanyl)-2-phenylimidazo[1,2-a]pyridine (5g). White solid, mp 49.1-51.6 °C. Yield: 0.074 g (38%);
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NMR H (CDCl3, 400 MHz): δ = 8.1 – 8.0 (m, 3H), 7.7 (dt, J 9.0, 1.2 Hz, 1H), 7.5 – 7.4 (m, 2H), 7.4 – 7.4 (m, 1H),
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3
7.2 – 7.2 (m, 1H), 6.8 – 6.7 (m, 3H), 2.2 (s, 6H), 2.2 (s, 3H); C (CDCl3, 100 MHz): δ = 150.0, 146.8, 141.3, 138.0,
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34.1, 129.4, 129.0, 128.1, 128.1, 126.2, 125.4, 125.4, 117.3, 112.6, 104.6, 23.6, 20.7 . MS: m/z (rel. int.) 392
+
(
28), 312 (100), 193 (8.2), 78 (39). HRMS: Calcd. for C22H20N2Se: [M+H] : 393.0865 found: 393.0865.
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3-(Butylselanyl)-2-phenylimidazo[1,2-a]pyridine (5h). Brown oil. Yield: 0.139 g (81%); H NMR (CDCl3, 400
MHz): δ = 8.52 (d, J 6.8 Hz, 1H), 8.23 (d, J 7.5 Hz, 2H), 7.66 (d, J 9.0 Hz, 1H), 7.45 (t, J 7.6 Hz, 2H), 7.35 (t, J 7.3
Hz, 1H), 7.26 – 7.22 (m, 1H), 6.87 (t, J 6.7 Hz, 1H), 2.64 (t, J 7.3 Hz, 2H), 1.45 (quint, J 7.2 Hz, 2H), 1.27 (sext, J
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3
7
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.3 Hz, 2H), 0.74 (t, J 7.3 Hz, 3H). C NMR (CDCl3, 100 MHz): δ = 150.1, 147.0, 134.0, 128.6, 128.0, 127.9, 125.7,
25.4, 117.3, 112.5, 104.2, 31.9, 29.1, 22.5, 13.3.MS: m/z (rel. int.) 330 (44.0), 288 (100.0), 194 (11.3), 78
(
75.3).
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-(4-Chlorophenyl)-3-(phenylselanyl)imidazo[1,2-a]pyridine (5i). Yellow solid, mp 81.1-83.4 °C; Yield: 0,103 g
1
(
54%); NMR H (CDCl3, 400 MHz): δ = 8.4 (dt, J 6.9, 1.2 Hz, 1H), 8.2 – 8.1 (m, 2H), 7.7 (dt, J 9.0, 1.1 Hz, 1H), 7.4
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3
–
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7.4 (m, 2H), 7.4 – 7.3 (m, 1H), 7.2 – 7.1 (m, 3H), 7.1 – 7.1 (m, 2H), 6.9 (td, J 6.8, 1.2 Hz, 1H). NMR C (CDCl3,
00 MHz): δ = 150.6, 147.8, 134.5, 132.3, 130.6, 130.0, 129.8, 128.6, 128.2, 126.8, 126.7, 125.6, 117.5, 113.2,
03.0. MS: m/z (rel. int.) 384 (41.8), 304 (100.0), 193 (1.8), 78 (83.8).
-(4-Fluorophenyl)-3-(phenylselanyl)imidazo[1,2-a]pyridine (5j). Yellow solid, mp 99.5-101.3 °C Yield: 0.105 g
1
(
57%); H NMR (CDCl3, 400 MHz): δ = 8.36 (dt, J 6.9, 1.1 Hz, 1H), 8.21 – 8.16 (m, 2H), 7.71 (dt, J 9.0, 1.1 Hz, 1H),
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3
1
7
=
1
.33 – 7.28 (m, 1H), 7.20 – 7.10 (m, 7H), 6.85 (td, J 6.8, 1.2 Hz, 1H). C NMR (CDCl3, 100 MHz): δ = 163.0 (d, JC-F
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248.1 Hz), 150.8, 147.7, 130.7, 130.5 (d, JC-F = 8.1 Hz), 130.0 (d, JC-F = 3.2 Hz), 129.7, 128.2, 126.7, 126.4,
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25.5, 117.4, 115.2 (d, JC-F = 21.3 Hz), 113.0, 102.7. MS: m/z (rel. int.) 368 (35.5), 288 (100.0), 211 (7.5), 78
(
77.2).
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-(4-Nitrophenyl)-3-(phenylselanyl)imidazo[1,2-a]pyridine (5l). Yellow solid, mp 154.4-156.4 °C. Yield: 0,0967
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g (49%); NMR H (CDCl3, 400 MHz): δ = 8.4 – 8.3 (m, 3H), 8.2 – 8.1 (m, 2H), 7.6 (dt, J 9.0, 1.1 Hz, 1H), 7.3 – 7.2
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(
m, 1H), 7.1 – 7.1 (m, 3H), 7.1 – 7.0 (m, 2H), 6.8 (td, J 6.8, 1.2 Hz, 1H). NMR C (CDCl3, 100 MHz): δ = 148.9,
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47.9, 147.5, 140.2, 130.1, 129.9, 129.2, 128.3, 127.2, 127.1, 125.7, 123.5, 117.8, 113.6, 104.6. MS: m/z (rel.
+
int.) 395 (16.5), 315 (69), 193 (2.8), 78 (100). HRMS: Calcd. For C19H14N3O2Se: [M+H] : 396.0246 found:
396.0380.
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-(Phenylselanyl)-2-(p-tolyl)imidazo[1,2-a]pyridine (5m). White solid, mp 65-66 °C; Yield: 0.131 g (72%); NMR
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H (CDCl3, 400 MHz): δ = 8.4 (dt, J 6.8, 1.2 Hz, 1H), 8.1 (d, J 8.2 Hz, 2H), 7.7 (d, J 9.0 Hz, 1H), 7.4 – 7.2 (m, 3H),
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7.2 – 7.2 (m, 3H), 7.1 (dt, J 6.8, 2.4 Hz, 2H), 6.9 (td, J 6.8, 1.2 Hz, 1H), 2.4 (s, 3H). NMR C (CDCl3, 100 MHz): δ =
151.8, 147.6, 138.3, 130.9, 130.8, 129.6, 129.0, 128.5, 128.1, 126.6, 126.3, 125.5, 117.3, 112.8, 102.4, 21.3
.
2
(
MS: m/z (rel. int.) 364 (34.2), 284 (100), 193 (1.1), 78 (64.3).
-(4-Methoxyphenyl)-3-(phenylselanyl)imidazo[1,2-a]pyridine (5n). Yellow oil, yield: 0.133 g (70%); H NMR
CDCl3, 400 MHz): δ = 8.30 (d, J 6.8 Hz, 1H), 8.13 (d, J 8.8 Hz, 2H), 7.67 (d, J 9.0 Hz, 1H), 7.26 – 7.22 (m, 1H),
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