Polycyclic N-heterocyclic compounds. Part 52. One-step syntheses of imidazo[1,5-a]pyridines, imidazo[1,5-a]quinolines and imidazo[5,1-a]isoquinolines by Vilsmeier reactions of pyridine-2-carbonitriles, quinoline-2-carbonitriles and isoquinoline-1-carbonitriles

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 22, 1998, Pages 3851-3856

  Sasaki, Kenji ^a   Tsurumori, Akifumi ^a   Hirota, Takashi ^a  

^a OKAYAMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748725200     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a804340j     Document Type: Article

References (27)

1. Part 51, K. Sasaki, T. Arichi, H. Ohtomo, T. Nakayama and T. Hirota, J. Heterocycl. Chem., 1996, 33, 1663.
2. O. Meth-Cohn and B. Tarnowski, Advances in Heterocyclic Chemistry: Cyclization under Vilsmeier Conditions, ed. A. R. Katritzky, Academic Press, New York, 1982, vol. 31, pp. 207-236.
3. T. Koyama, T. Horita, Y. Shinohara, M. Yamato and S. Ohmori, Chem. Pharm. Bull., 1975, 23, 497;
4. T. Hirota, T. Koyama, T. Namba and M. Yamato, Chem. Pharm. Bull., ibid., 1977, 25, 2838.
5. T. Hirota, H. Fujita, K. Sasaki, T. Nambda and S. Hayakawa, J. Heterocycl. Chem., 1986, 23, 1347.
6. T. Hirota, H. Fujita, K. Sasaki, T. Namba and S. Hayakawa, Heterocycles, 1986, 24, 771.
7. T. Hirota, H. Fujita, K. Sasaki and T. Namba, J. Heterocycl. Chem., 1986, 23, 1715.
8. T. Hirota, Y. Tashima, K. Sasaki, T. Namba and S. Hayakawa, Heterocycles, 1987, 26, 2717.
9. J. D. Bower and G. R. Ramage, J. Chem. Soc., 1955, 2834.
10. P. Blatcher and D. Middlemiss, Tetrahedron Lett., 1980, 21, 2195.
11. W. W. Paudler, C. I. P. Chao and L. S. Helmick, J. Heterocycl. Chem., 1972, 9, 1157.
12. O. Fuentes and W. W. Paudler, J. Heterocycl. Chem., 1975, 12, 379.
13. N. F. Ford, L. J. Browne, T. Campbell, C. Gemenden, R. Goldstein, C. Gude and J. W. F. Wasley, J. Med. Chem., 1985, 28, 164.
14. Y. Cheng, S. Goon and O. Meth-Cohn, Chem. Commun., 1996, 1395.
15. K. Sasaki, A. Tsurumori, S. Kashino and T. Hirota, Heterocycles, in press.
16. C. A. R. Baxter and K. Sandwich, Ger. Offen., 2 007 345, 1970 (Chem. Abstr., 1970, 73, 109784s).
17. E. Pretsch, T. Clerc, J. Seibl and W. Simon, Table of Spectral Data for Structure Determination of Organic Compounds, in Proton Resonance Spectroscopy, ed. W. Fresenius, J. F. Huber, E. Pungor, G. A. Rechnitz, W. Simon and T. S. West, Springer-Verlag, Berlin, 1989, pp. H265-H325.
18. For 8; W. E. Feely and E. M. Beavers, J. Am. Chem. Soc., 1959, 81, 4004.
19. For 12; F. Montanari and L. Pentimalli, Gazz. Chim. Ital., 1953, 83, 273.
20. T. Sakamoto, S. Kanda, S. Nishimura and H. Yamanaka, Chem. Pharm. Bull., 1985, 33, 565.
21. J. Ciernik, Collect. Czech. Chem. Commun., 1972, 37, 2273.
22. G. W. Kirby, S. L. Tan and B. C. Uff, J. Chem. Soc., Perkin Trans. 1, 1979, 270.
23. H. Reimlinger, J. J. M. Vandewalle, W. R. F. Lingier and E. de Ruiter, Chem. Ber., 1975, 108, 3771.
24. O. Buchardt, J. Becher and C. Lohse, Acta Chem. Scand., 1965, 19, 1120.
25. E. Ochiai and H. Tonida, Chem. Pharm. Bull., 1957, 5, 621.
26. E. Ochiai, M. Ishikawa and S. Zai-Ren, J. Pharm. Soc. Jpn., 1944, 64, 72.
27. M. M. Robison and B. L. Robison, J. Org. Chem., 1956, 21, 1337.