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11. (a) Miyashita, M. K.; Toshiaki; Yoshikoshi, A. J. Chem.
Soc., Chem. Commun. 1978, 8, 362; (b) Kulinkovich, O.
G.; Tishchenko, I. G.; Roslik, N. A. Zh. Org. Khim.
1984, 20, 532; (c) Chan, W. H.; Lee, A. W. M.; Chan,
E. T. T. J. Chem. Soc., Perkin Trans. 1 1992, 945.
12. (a) Friedman, B. S.; Sparks, M.; Adams, R. J. Am.
Chem. Soc. 1937, 59, 2262; (b) Hantzsch, A. Chem. Ber.
1888, 21, 943; (c) Lewy, M. Chem. Ber. 1888, 21, 2193;
(d) Lewy, M. Chem. Ber. 1887, 20, 2576.
m), 7.74–7.70 (2H, m), 7.41 (1H, s), 7.28–7.20 (5H, m),
5.21–5.18 (1H, d, J=10 Hz), 3.15 (1H, m), 1.15–1.13
(3H, d, J=6 Hz), 0.98–0.96 (3H, d, J=6 Hz). 13C NMR
(75 MHz, CDCl3) l 167.4, 162.2, 158.3, 142.5, 141.1,
139.2, 135.9, 134.3, 131.5, 130.5, 129.3, 128.9, 128.5,
127.2, 123.6, 107.4, 54.0, 28.7, 20.6, 19.3. HRMS (CI)
calculated for C24H20N3O4S (MH+) 446.4994, found
446.1175.
17. Yellow oil. IR (film) 1561, 1480 cm−1 1H (300 MHz,
.
CDCl3) l 7.03–7.16 (5H, m), 2.3 (3H, s), 2.1 (3H, s). 13C
(75 MHz, CDCl3) l 164.0, 144.7, 136.2, 135.4, 129.2,
127.4, 126.5, 14.4, 12.0. HRMS (CI) calculated for
C11H12NOS (MH+) 206.0639, found 206.0631.
13. (a) Vinogradova, T. K.; Kisilenko, A. A.; Drach, B. S.
J. Org. Chem. USSR 1982, 18, 1630; (b) Matsumura,
K.; Miyashita, O.; Shimadzu, H.; Hashimoto, N. Chem.
Pharm. Bull. (Tokyo) 1976, 24, 948; (c) Dewar, M. J. S.;
Turchi, I. J. J. Org. Chem. 1975, 40, 1521; (d) Masaak,
M.; Kumazawa, T.; Yoshikoshi, A. J. Chem. Soc.,
Chem. Commun. 1978, 362; (e) Burger, K.; Hu¨bl, D.;
Geith, K. Synthesis 1988, 194; (f) Jenny, C.; Heimgart-
ner, H. Helv. Chim. Acta 1989, 1639.
1
18. Mp 33–35°C. IR (film) 1542, 1476 cm−1. H NMR (300
MHz, CDCl3) l 9.29–9.26 (1H, d, J=8 Hz), 8.25–8.23
(1H, d, J=7 Hz), 7.99–7.97 (1H, d, J=8 Hz), 7.93–7.90
(1H, d, J=7 Hz), 7.41–7.68 (4H, m), 7.23–7.40 (5H, m).
13C NMR (75 MHz, CDCl3) l 165.3, 141.9, 135.9,
134.1, 132.2, 130.2, 129.5, 129.4, 129.0, 128.5, 127.9,
127.4, 126.5, 126.0, 125.1, 124.8, 123.6. HRMS (CI)
calculated for C19H14NOS (MH+) 304.0796, found
304.0797.
1
14. Mp 87–89°C. IR (film) 1552, 1486 cm−1. H NMR (300
MHz, CDCl3) l 8.08 (6H, m), 7.52 (9H, m). 13C NMR
(75 MHz, CDCl3) l 159.8, 134.4, 130.9, 130.1, 129.0,
128.7, 128.4, 127.0, 126.9, 126.8, 126.5, 126.4. HRMS
(CI) calculated for C15H12NOS (MH+) 330.0952, found
330.0951.
1
19. Mp 59–61°C. IR (film) 1750, 1620, 1581, 1454 cm−1. H
NMR (300 MHz, CDCl3) l 8.21–8.33 (3H, m), 7.51
(1H, s), 7.22–7.49 (7H, m), 4.11 (3H, s). 13C NMR (75
MHz, CDCl3) l 141.0, 136.0, 135.6, 134.7, 129.5, 129.1,
128.4, 127.7, 127.2, 126.6, 126.0, 125.7, 124.4, 121.7,
115.3, 110.0, 54.9. HRMS (CI) calculated for
C19H15N2O3S (MH+) 351.0803, found 351.0797.
20. Desulfurization of 2-phenyl-5-thiophenyloxazole with
deactivated Raney nickel in acetone gave 2-phenyloxa-
zole (67%).
15. Mp 63.5–64.5°C. IR (film) 1546, 1476 cm−1 1H NMR
.
(300 MHz, CDCl3) l 8.05–8.08 (2H, m), 7.46–7.48 (4H,
m), 7.23–7.31 (5H, m). 13C NMR (75 MHz, CDCl3) l
165.3, 142.0, 136.3, 134.6, 131.1, 129.5, 129.0, 128.5,
127.2, 126.7. HRMS (CI) calculated for C15H12NOS
(MH+) 254.0639, found 254.0634.
1
16. Mp 77–79°C. IR (film) 1769, 1717, 1582, 1466 cm−1. H
NMR (300 MHz, CDCl3) l 8.16 (1H, s), 7.83–7.80 (2H,