A novel reaction of benzoyl chloride adduct of aromatic N-oxide with carbonitrile via a carbene intermediate

Tetrahedron Letters

Volumn 37, Issue 1, 1996, Pages 69-72

  Tagawa, Yoshinobu ^a   Tanaka, Jun'ichi ^a   Hama, Kazuya ^a   Goto, Yoshinobu ^a   Hamana, Masatomo ^b  

^a FUKUOKA UNIVERSITY   (Japan)

^b CHUGAI PHARMACEUTICAL CO LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; PYRIDINE DERIVATIVE; QUINOLINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0030023329     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02104-3     Document Type: Article

References (15)

1. a) Y. Tagawa, K. Hama, Y. Goto, and M. Hamana, Heterocycles, 1992, 34, 2243.
2. b) ibid., 1995, 40, 809.
3. -1. The structure of 2 was further confirmed by its synthesis in 29% yield from 2-benzoylaminoquinoline with trimethylsilylurethane-acetylchloirde (a) N. Ya. Derkach and N. P. Smetankina, Zhurnal Obshchei Khimii, 1964, 34, 3613.
4. b) L. M. Weinstock, S. Karady, F. E. Roberts, A. M. Hoinowski, G. S. Brenner, T. B. K. Lee, W. C. Lumma and M. Sletzinger, Tetrahedron Letters, 1975, 3979).
5. F. M. Hamer, J. Chem. Soc., 1924, 125, 1348.
6. -1.
7. -1.
8. E. H. Huntress and H. C. Walter, J. Org. Chem., 1948, 13, 735.
9. D. St. C. Black and R. C. Srivastava, Aust. J. Chem., 1971, 24, 287. Whereas D. St. C. Black reported that the melting point of N, N -bis(2-pyridyl)-benzamide is 89-90 °C, the compound we prepared according to their synthetic method indicates the melting point of 160-161 °C, which completely coincided with the melting point of our product obtained in the present experiment.
10. a) S. Oae and S. Kozuka, Tetrahedron, 1964, 20, 2671 .
11. b) S. Oae and K. Ogino, Heterocycles, 1977, 6, 583.
12. a) T. Umemoto and G. Tomizawa, Tetrahedron Lett., 1987, 28, 2705.
13. b) T. Umemoto and G. Tomizawa, J. Org. Chem., 1989, 54, 1726 .
14. c) A. S. Kiselyov and L. Strekowski, Terahedron Lett., 1994, 35, 207 .
15. For example, M. Van Der Puy, D. Nalewajek, and G. E. Wicks, Tetrahedron Lett., 1988, 29, 4389 and references cited therein.