Preparation of New Nitrogen-Bridged Heterocycles. 42.1 Synthesis and the Reaction of Pyridinium N-Ylides Using Bifunctional Ethyl Thiocyanatoacetates

Bulletin of the Chemical Society of Japan

Volumn 69, Issue 6, 1996, Pages 1769-1776

  Kakehi, Akikazu ^a   Ito, Suketaka ^a   Hashimoto, Yasunobu ^a  

^a SHINSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0038818437     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.69.1769     Document Type: Article

References (45)

1. For part 41 of this series, see : A. Kakehi, S. Ito, and F. Ishida, Heterocycles, 41, 2657 (1995).
2. For reviews of this type of reaction, see : R. Huisgen, R. Grashey, and J. Sauer, "The Chemistry of Alkenes," ed by S. Patai, Interscience, New York, N. Y. (1964), Chap. 11, p. 739; C. G. Stuckwisch, Synthesis, 1973, 469; H-J. Timpe, "Advances in Heterocyclic Chemistry," ed by A. R. Katritzky and A. J. Boulton, Academic Press, New York (1974), Vol. 17, p. 213; F. J. Swinbourne, J. H. Hunt, and G. Klinkert, "Advances in Heterocyclic Chemistry," ed by A. R. Katritzky and A. J. Boulton, Academic Press, New York (1978), Vol. 23, p. 103; T. Uchida and K. Matsumoto, Synthesis, 1976, 209.
3. For reviews of this type of reaction, see : R. Huisgen, R. Grashey, and J. Sauer, "The Chemistry of Alkenes," ed by S. Patai, Interscience, New York, N. Y. (1964), Chap. 11, p. 739; C. G. Stuckwisch, Synthesis, 1973, 469; H-J. Timpe, "Advances in Heterocyclic Chemistry," ed by A. R. Katritzky and A. J. Boulton, Academic Press, New York (1974), Vol. 17, p. 213; F. J. Swinbourne, J. H. Hunt, and G. Klinkert, "Advances in Heterocyclic Chemistry," ed by A. R. Katritzky and A. J. Boulton, Academic Press, New York (1978), Vol. 23, p. 103; T. Uchida and K. Matsumoto, Synthesis, 1976, 209.
4. For reviews of this type of reaction, see : R. Huisgen, R. Grashey, and J. Sauer, "The Chemistry of Alkenes," ed by S. Patai, Interscience, New York, N. Y. (1964), Chap. 11, p. 739; C. G. Stuckwisch, Synthesis, 1973, 469; H-J. Timpe, "Advances in Heterocyclic Chemistry," ed by A. R. Katritzky and A. J. Boulton, Academic Press, New York (1974), Vol. 17, p. 213; F. J. Swinbourne, J. H. Hunt, and G. Klinkert, "Advances in Heterocyclic Chemistry," ed by A. R. Katritzky and A. J. Boulton, Academic Press, New York (1978), Vol. 23, p. 103; T. Uchida and K. Matsumoto, Synthesis, 1976, 209.
5. For reviews of this type of reaction, see : R. Huisgen, R. Grashey, and J. Sauer, "The Chemistry of Alkenes," ed by S. Patai, Interscience, New York, N. Y. (1964), Chap. 11, p. 739; C. G. Stuckwisch, Synthesis, 1973, 469; H-J. Timpe, "Advances in Heterocyclic Chemistry," ed by A. R. Katritzky and A. J. Boulton, Academic Press, New York (1974), Vol. 17, p. 213; F. J. Swinbourne, J. H. Hunt, and G. Klinkert, "Advances in Heterocyclic Chemistry," ed by A. R. Katritzky and A. J. Boulton, Academic Press, New York (1978), Vol. 23, p. 103; T. Uchida and K. Matsumoto, Synthesis, 1976, 209.
6. For reviews of this type of reaction, see : R. Huisgen, R. Grashey, and J. Sauer, "The Chemistry of Alkenes," ed by S. Patai, Interscience, New York, N. Y. (1964), Chap. 11, p. 739; C. G. Stuckwisch, Synthesis, 1973, 469; H-J. Timpe, "Advances in Heterocyclic Chemistry," ed by A. R. Katritzky and A. J. Boulton, Academic Press, New York (1974), Vol. 17, p. 213; F. J. Swinbourne, J. H. Hunt, and G. Klinkert, "Advances in Heterocyclic Chemistry," ed by A. R. Katritzky and A. J. Boulton, Academic Press, New York (1978), Vol. 23, p. 103; T. Uchida and K. Matsumoto, Synthesis, 1976, 209.
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9. T. Okamoto, M. Hirobe, and T. Yamazaki, Chem. Pharm. Bull., 14, 512 (1966); Y. Tamura, A. Yamakami, and M. Ikeda, Yakugaku Zasshi, 91, 1154 (1971); Y. Tamura, N. Tsujimoto, Y. Sumida, and M. Ikeda, Tetrahedron, 28, 21 (1972); T. Sasaki, K. Kanematsu, and A. Kakehi, J. Org. Chem., 37, 3106 (1972); Y. Tamura, Y. Sumida, and M. Ikeda, J. Chem. Soc., Perkin Trans. 1, 1973, 2091; Y. Tamura, Y. Sumida, S. Haruki, and M. Ikeda, J. Chem. Soc., Perkin Trans. 1, 1975, 575; A. Kakehi, S. Ito, T. Funahashi, and Y. Ota, J. Org. Chem., 41, 1570 (1976); A. Kakehi, S. Ito, K. Uchiyama, Y. Konno, and K. Kondo, J. Org. Chem., 42, 443 (1977); Y. Tominaga, Y. Miyake, H. Fujito, K. Kurata, H. Awaya, Y. Matsuda, and G. Kobayashi, Chem. Pharm. Bull., 25, 1528 (1977).
10. T. Okamoto, M. Hirobe, and T. Yamazaki, Chem. Pharm. Bull., 14, 512 (1966); Y. Tamura, A. Yamakami, and M. Ikeda, Yakugaku Zasshi, 91, 1154 (1971); Y. Tamura, N. Tsujimoto, Y. Sumida, and M. Ikeda, Tetrahedron, 28, 21 (1972); T. Sasaki, K. Kanematsu, and A. Kakehi, J. Org. Chem., 37, 3106 (1972); Y. Tamura, Y. Sumida, and M. Ikeda, J. Chem. Soc., Perkin Trans. 1, 1973, 2091; Y. Tamura, Y. Sumida, S. Haruki, and M. Ikeda, J. Chem. Soc., Perkin Trans. 1, 1975, 575; A. Kakehi, S. Ito, T. Funahashi, and Y. Ota, J. Org. Chem., 41, 1570 (1976); A. Kakehi, S. Ito, K. Uchiyama, Y. Konno, and K. Kondo, J. Org. Chem., 42, 443 (1977); Y. Tominaga, Y. Miyake, H. Fujito, K. Kurata, H. Awaya, Y. Matsuda, and G. Kobayashi, Chem. Pharm. Bull., 25, 1528 (1977).
11. T. Okamoto, M. Hirobe, and T. Yamazaki, Chem. Pharm. Bull., 14, 512 (1966); Y. Tamura, A. Yamakami, and M. Ikeda, Yakugaku Zasshi, 91, 1154 (1971); Y. Tamura, N. Tsujimoto, Y. Sumida, and M. Ikeda, Tetrahedron, 28, 21 (1972); T. Sasaki, K. Kanematsu, and A. Kakehi, J. Org. Chem., 37, 3106 (1972); Y. Tamura, Y. Sumida, and M. Ikeda, J. Chem. Soc., Perkin Trans. 1, 1973, 2091; Y. Tamura, Y. Sumida, S. Haruki, and M. Ikeda, J. Chem. Soc., Perkin Trans. 1, 1975, 575; A. Kakehi, S. Ito, T. Funahashi, and Y. Ota, J. Org. Chem., 41, 1570 (1976); A. Kakehi, S. Ito, K. Uchiyama, Y. Konno, and K. Kondo, J. Org. Chem., 42, 443 (1977); Y. Tominaga, Y. Miyake, H. Fujito, K. Kurata, H. Awaya, Y. Matsuda, and G. Kobayashi, Chem. Pharm. Bull., 25, 1528 (1977).
12. T. Okamoto, M. Hirobe, and T. Yamazaki, Chem. Pharm. Bull., 14, 512 (1966); Y. Tamura, A. Yamakami, and M. Ikeda, Yakugaku Zasshi, 91, 1154 (1971); Y. Tamura, N. Tsujimoto, Y. Sumida, and M. Ikeda, Tetrahedron, 28, 21 (1972); T. Sasaki, K. Kanematsu, and A. Kakehi, J. Org. Chem., 37, 3106 (1972); Y. Tamura, Y. Sumida, and M. Ikeda, J. Chem. Soc., Perkin Trans. 1, 1973, 2091; Y. Tamura, Y. Sumida, S. Haruki, and M. Ikeda, J. Chem. Soc., Perkin Trans. 1, 1975, 575; A. Kakehi, S. Ito, T. Funahashi, and Y. Ota, J. Org. Chem., 41, 1570 (1976); A. Kakehi, S. Ito, K. Uchiyama, Y. Konno, and K. Kondo, J. Org. Chem., 42, 443 (1977); Y. Tominaga, Y. Miyake, H. Fujito, K. Kurata, H. Awaya, Y. Matsuda, and G. Kobayashi, Chem. Pharm. Bull., 25, 1528 (1977).
13. T. Okamoto, M. Hirobe, and T. Yamazaki, Chem. Pharm. Bull., 14, 512 (1966); Y. Tamura, A. Yamakami, and M. Ikeda, Yakugaku Zasshi, 91, 1154 (1971); Y. Tamura, N. Tsujimoto, Y. Sumida, and M. Ikeda, Tetrahedron, 28, 21 (1972); T. Sasaki, K. Kanematsu, and A. Kakehi, J. Org. Chem., 37, 3106 (1972); Y. Tamura, Y. Sumida, and M. Ikeda, J. Chem. Soc., Perkin Trans. 1, 1973, 2091; Y. Tamura, Y. Sumida, S. Haruki, and M. Ikeda, J. Chem. Soc., Perkin Trans. 1, 1975, 575; A. Kakehi, S. Ito, T. Funahashi, and Y. Ota, J. Org. Chem., 41, 1570 (1976); A. Kakehi, S. Ito, K. Uchiyama, Y. Konno, and K. Kondo, J. Org. Chem., 42, 443 (1977); Y. Tominaga, Y. Miyake, H. Fujito, K. Kurata, H. Awaya, Y. Matsuda, and G. Kobayashi, Chem. Pharm. Bull., 25, 1528 (1977).
14. T. Okamoto, M. Hirobe, and T. Yamazaki, Chem. Pharm. Bull., 14, 512 (1966); Y. Tamura, A. Yamakami, and M. Ikeda, Yakugaku Zasshi, 91, 1154 (1971); Y. Tamura, N. Tsujimoto, Y. Sumida, and M. Ikeda, Tetrahedron, 28, 21 (1972); T. Sasaki, K. Kanematsu, and A. Kakehi, J. Org. Chem., 37, 3106 (1972); Y. Tamura, Y. Sumida, and M. Ikeda, J. Chem. Soc., Perkin Trans. 1, 1973, 2091; Y. Tamura, Y. Sumida, S. Haruki, and M. Ikeda, J. Chem. Soc., Perkin Trans. 1, 1975, 575; A. Kakehi, S. Ito, T. Funahashi, and Y. Ota, J. Org. Chem., 41, 1570 (1976); A. Kakehi, S. Ito, K. Uchiyama, Y. Konno, and K. Kondo, J. Org. Chem., 42, 443 (1977); Y. Tominaga, Y. Miyake, H. Fujito, K. Kurata, H. Awaya, Y. Matsuda, and G. Kobayashi, Chem. Pharm. Bull., 25, 1528 (1977).
15. T. Okamoto, M. Hirobe, and T. Yamazaki, Chem. Pharm. Bull., 14, 512 (1966); Y. Tamura, A. Yamakami, and M. Ikeda, Yakugaku Zasshi, 91, 1154 (1971); Y. Tamura, N. Tsujimoto, Y. Sumida, and M. Ikeda, Tetrahedron, 28, 21 (1972); T. Sasaki, K. Kanematsu, and A. Kakehi, J. Org. Chem., 37, 3106 (1972); Y. Tamura, Y. Sumida, and M. Ikeda, J. Chem. Soc., Perkin Trans. 1, 1973, 2091; Y. Tamura, Y. Sumida, S. Haruki, and M. Ikeda, J. Chem. Soc., Perkin Trans. 1, 1975, 575; A. Kakehi, S. Ito, T. Funahashi, and Y. Ota, J. Org. Chem., 41, 1570 (1976); A. Kakehi, S. Ito, K. Uchiyama, Y. Konno, and K. Kondo, J. Org. Chem., 42, 443 (1977); Y. Tominaga, Y. Miyake, H. Fujito, K. Kurata, H. Awaya, Y. Matsuda, and G. Kobayashi, Chem. Pharm. Bull., 25, 1528 (1977).
16. T. Eicher and A. Hansen, Tetrahedron Lett., 1967, 1169; T. Sasaki, K. Kanematsu, and A. Kakehi, J. Org. Chem., 36, 2451 (1971); J. W. Lown and K. Matsumoto, Can. J. Chem., 50, 584 (1972); C. W. Rees and E. von Angerer, J. Chem. Soc., Chem. Commun., 1972, 420; O. Tsuge, H. Shimoharada, and M. Noguchi, Chem. Lett., 1981, 1199; K. Matsumoto, T. Uchida, Y. Yagi, H. Tahara, and R. M. Acheson, Heterocycles, 23, 2041 (1985).
17. T. Eicher and A. Hansen, Tetrahedron Lett., 1967, 1169; T. Sasaki, K. Kanematsu, and A. Kakehi, J. Org. Chem., 36, 2451 (1971); J. W. Lown and K. Matsumoto, Can. J. Chem., 50, 584 (1972); C. W. Rees and E. von Angerer, J. Chem. Soc., Chem. Commun., 1972, 420; O. Tsuge, H. Shimoharada, and M. Noguchi, Chem. Lett., 1981, 1199; K. Matsumoto, T. Uchida, Y. Yagi, H. Tahara, and R. M. Acheson, Heterocycles, 23, 2041 (1985).
18. T. Eicher and A. Hansen, Tetrahedron Lett., 1967, 1169; T. Sasaki, K. Kanematsu, and A. Kakehi, J. Org. Chem., 36, 2451 (1971); J. W. Lown and K. Matsumoto, Can. J. Chem., 50, 584 (1972); C. W. Rees and E. von Angerer, J. Chem. Soc., Chem. Commun., 1972, 420; O. Tsuge, H. Shimoharada, and M. Noguchi, Chem. Lett., 1981, 1199; K. Matsumoto, T. Uchida, Y. Yagi, H. Tahara, and R. M. Acheson, Heterocycles, 23, 2041 (1985).
19. T. Eicher and A. Hansen, Tetrahedron Lett., 1967, 1169; T. Sasaki, K. Kanematsu, and A. Kakehi, J. Org. Chem., 36, 2451 (1971); J. W. Lown and K. Matsumoto, Can. J. Chem., 50, 584 (1972); C. W. Rees and E. von Angerer, J. Chem. Soc., Chem. Commun., 1972, 420; O. Tsuge, H. Shimoharada, and M. Noguchi, Chem. Lett., 1981, 1199; K. Matsumoto, T. Uchida, Y. Yagi, H. Tahara, and R. M. Acheson, Heterocycles, 23, 2041 (1985).
20. T. Eicher and A. Hansen, Tetrahedron Lett., 1967, 1169; T. Sasaki, K. Kanematsu, and A. Kakehi, J. Org. Chem., 36, 2451 (1971); J. W. Lown and K. Matsumoto, Can. J. Chem., 50, 584 (1972); C. W. Rees and E. von Angerer, J. Chem. Soc., Chem. Commun., 1972, 420; O. Tsuge, H. Shimoharada, and M. Noguchi, Chem. Lett., 1981, 1199; K. Matsumoto, T. Uchida, Y. Yagi, H. Tahara, and R. M. Acheson, Heterocycles, 23, 2041 (1985).
21. T. Eicher and A. Hansen, Tetrahedron Lett., 1967, 1169; T. Sasaki, K. Kanematsu, and A. Kakehi, J. Org. Chem., 36, 2451 (1971); J. W. Lown and K. Matsumoto, Can. J. Chem., 50, 584 (1972); C. W. Rees and E. von Angerer, J. Chem. Soc., Chem. Commun., 1972, 420; O. Tsuge, H. Shimoharada, and M. Noguchi, Chem. Lett., 1981, 1199; K. Matsumoto, T. Uchida, Y. Yagi, H. Tahara, and R. M. Acheson, Heterocycles, 23, 2041 (1985).
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28. Some reactions of 3,5-lutidinium dicyanomethylide (6c) are already reported, but its physical and spectral data are not shown: K. Matsumoto and T. Uchida, Synthesis, 1978, 207; K. Matsumoto, T. Uchida, and L. A. Paquette, Synthesis, 1979, 746; K. Matsumoto and T. Uchida, J. Chem. Soc., Perkin Trans. 1, 1981, 73; K. Matsumoto, T. Uchida, Y. Ikemi, T. Tanaka, M. Asahi, T. Kato, and H. Konishi, Bull. Chem. Soc. Jpn., 60, 3645 (1987).
29. Some reactions of 3,5-lutidinium dicyanomethylide (6c) are already reported, but its physical and spectral data are not shown: K. Matsumoto and T. Uchida, Synthesis, 1978, 207; K. Matsumoto, T. Uchida, and L. A. Paquette, Synthesis, 1979, 746; K. Matsumoto and T. Uchida, J. Chem. Soc., Perkin Trans. 1, 1981, 73; K. Matsumoto, T. Uchida, Y. Ikemi, T. Tanaka, M. Asahi, T. Kato, and H. Konishi, Bull. Chem. Soc. Jpn., 60, 3645 (1987).
30. Some reactions of 3,5-lutidinium dicyanomethylide (6c) are already reported, but its physical and spectral data are not shown: K. Matsumoto and T. Uchida, Synthesis, 1978, 207; K. Matsumoto, T. Uchida, and L. A. Paquette, Synthesis, 1979, 746; K. Matsumoto and T. Uchida, J. Chem. Soc., Perkin Trans. 1, 1981, 73; K. Matsumoto, T. Uchida, Y. Ikemi, T. Tanaka, M. Asahi, T. Kato, and H. Konishi, Bull. Chem. Soc. Jpn., 60, 3645 (1987).
31. Some reactions of 3,5-lutidinium dicyanomethylide (6c) are already reported, but its physical and spectral data are not shown: K. Matsumoto and T. Uchida, Synthesis, 1978, 207; K. Matsumoto, T. Uchida, and L. A. Paquette, Synthesis, 1979, 746; K. Matsumoto and T. Uchida, J. Chem. Soc., Perkin Trans. 1, 1981, 73; K. Matsumoto, T. Uchida, Y. Ikemi, T. Tanaka, M. Asahi, T. Kato, and H. Konishi, Bull. Chem. Soc. Jpn., 60, 3645 (1987).
32. According to our private communication, Dr. K. Matsumoto and co-workers are now preparing the paper (the contribution to J. Heterocycl. Chem. is expected) on the syntheses of various azinium ylides involving 6c (mp 256-257 °C).
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41. For bond dissociation energy, see : "Kagaku Binran," 3rd ed, ed by the Chemical Society of Japan, Maruzen, Tokyo (1984), p. II-324.
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