A novel route to disubstituted [7]thiaheterohelicene via biaryl- and carbonyl-coupling reactions

Tetrahedron Letters

Volumn 38, Issue 3, 1997, Pages 457-460

  Tanaka, Kazuhiko ^a   Suzuki, Hitomi ^a   Osuga, Hideji ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; THIOPHENE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0031012867     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02325-8     Document Type: Article

References (42)

1. (a) Ashitaka, H.; Yokoh, Y.; Shimizu, R.; Yokozawa, T.; Morita, K.; Suehiro, T.; Matsumoto, Y. Nonlinear Optics, 1993, 4, 281-297;
2. (b) Morita, K.; Suehiro, T.; Yokoh, Y.; Ashitaka, H. J. Photopolymer Sci. Tec. 1993, 6, 229-238.
3. (a) Nakazaki, M.; Yamamoto, K.; Ikeda, T.; Kitsuki, T.; Okamoto, Y. J. Chem. Soc., Chem. Commun. 1983, 787-788;
4. (b) Yamamoto, K.; Ikeda, T.; Kitsuki, T.; Okamoto, Y.; Chikamatsu, H.; Nakazaki, M. J. Chem. Soc., Perkin 1, 1990, 271-276;
5. (c)Tanaka, K.; Osuga, H.; Shogase, Y.; Suzuki, H.; Nakanishi, W.; Nakamura, K.; Kawai, Y. J. Chem. Soc., Chem. Commun. 1995, 1873-1874.
6. (a) Meurer, K. P.; Vögtle, F. Top. Currn. Chem. 1985, 127, 1-76;
7. (b) Laarhoven, W. H.; Prinsen, W. J. C. Top. Currn. Chem. 1984, 125, 63-130;
8. (c)Martin, R. H. Angew. Chem., Int. Ed. Eng. 1974, 13, 649-660;
9. (d)Wynberg, H. Acc. Chem. Res. 1971, 4, 65-73.
10. Gilbert, A. M.; Katz, T. J.; Geiger, W. E.; Robben, M. P.; Rheingold, A. L. J. Am. Chem. Soc. 1993, 115, 3199-3211.
11. Mallory, F. B.; Mallory, C. W. Organic Reactions; Wiley & Sons: New York, 1984; Vol. 30, pp. 1-456.
12. Newman, M. S.; Lednicer, D. J. Am. Chem. Soc. 1956, 78, 4765-4770.
13. (a) Pereira, D. E.; Neelima; Leonard, N. J. Tetrahedron 1990, 46, 5895-5908;
14. (b) Larsen J.; Bechgaard, K. J. Org. Chem. 1996, 61, 1151-1152;
15. (c)Rau, H.; Schuster, O. Angew. Chem., Int. Ed. Eng. 1976, 15, 114-115.
16. (a) Bestmann, V. J.; Both, W. Angew. Chem. 1972, 84, 293;
17. (b) Stará, I. G.; Star'y, I.; Tich'y, M.; Závada, J.; Hanus, V. J. Am. Chem. Soc. 1994, 116, 5084-5088.
18. Dore, A.; Fabbri, D.; Gladiali, S.; Valle, G. Tetrahedron: Asymmetry 1995, 6, 779-788.
19. Fritsch, R.; Hartmann, E.; Andert, D.; Mannschreck, A. Chem. Ber. 1992, 125, 849-855.
20. (a) Högberg, H.-E. Acta Chem. Scand. 1973, 27, 2591-2596;
21. (b) Zander, M.; Franke, W. H. Chem. Ber. 1969, 102, 2728-2738;
22. (c)Bogaert-Verhoogen, D.; Martin, R. H. Tetrahedron Lett. 1967, 3045;
23. (d)Teuber, H.-J. Vogel, L. Chem. Ber. 1970, 103, 3319-3342;
24. (e) Bringmann, G.; Schöner, B.; Schupp, O.; Peters, K.; Peters, E.-M.; von Schnering, H. G. Liebigs Ann. Chem. 1994, 91-97.
25. (a) Nuckolls, C.; Katz, T. J.; Castellanos, L. J. Am. Chem. Soc. 1996, 118, 3767-3768;
26. (b) Willmore, N. D.; Hoic, D. A.; Katz, T. J. J. Org. Chem. 1994, 59, 1889-1891;
27. (c)Liu, L.; Katz, T. J. Tetrahedron Lett. 1990, 31, 3983-3986, and references cited therein;
28. Willmore, N. D.; Liu, L.; Katz, T. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 1093-1095.
29. Lehman, P. G.; Wynberg, H. Aust. J. Chem. 1974, 27, 315-322.
30. Comins, D. L.; Killpack, M. O. J. Org. Chem. 1987, 52, 104-109.
31. (a) Reuman, M.; Meyers, A. I. Tetrahedron 1985, 41, 837-860;
32. (b) Vecchia, L. D.; Vlattas, I. J. Org. Chem. 1977, 42, 2649-2650.
33. (a) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508-524;
34. (b) Crisp, G. T. Synth. Commun. 1989, 19, 307-316;
35. Gronowitz, G. J. Heterocycl. Chem. 1994, 31, 641-662.
36. (a) McMurry J. E. Chem. Rev. 1989, 89, 1513-1524;
37. (b) Hu, Z.; Cava, M. P. Tetrahedron Lett. 1994, 35, 3493-3496;
38. (c)Yoshida, S.; Fujii, M.; Aso, Y.; Otsubo, T.; Ogura, F. J. Org. Chem. 1994, 59, 3077-3081.
39. McMurry, J. E.; Lectka, T.; Rico, J. G. J. Org. Chem. 1989, 54, 3748-3749.
40. (a) Tanaka, K.; Kitahara, Y.; Suzuki, H.; Osuga, H.; Kawai Y. Tetrahedron Lett. 1996, 37, 5925-5928;
41. (b) Nakagawa, H.; Obata, A; Yamada, K.; Kawazura, H. J. Chem. Soc., Perkin. Trans. 2, 1985, 1899-1903;
42. (c)Yamada, K.; Ishii, R.; Nakagawa, H.; Kawazura, H. Tetrahedron: Asymmetry 1996, 7, 737-746.