Synthesis of Isoxazole Derivatives by Means of O-Acylation of Aliphatic Nitro Compounds in the Presence of Acetylenic Compounds

Chemical and Pharmaceutical Bulletin

Volumn 26, Issue 10, 1978, Pages 3254-3256

  Kaji, Eisuke ^a   Harada, Kazuho ^a   Zen, Shonosuke ^a  

^a KITASATO UNIVERSITY   (Japan)

Author keywords

1,3 dipolar cycloaddition; acetylenic compounds; aliphatic nitro compounds; dipolar aprotic solvent; fragmentation; isoxazole; nitrile oxide; O acylation

Indexed keywords

ISOXAZOLE DERIVATIVE;

2 BENZOYLOXYIMINO 2 CHLOROACETIC ACID METHYL ESTER; DRUG ANALYSIS; DRUG STRUCTURE; DRUG SYNTHESIS; IN VITRO STUDY; INFRARED SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; THEORETICAL STUDY;

EID: 0018086595     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.26.3254     Document Type: Article

References (14)

1. E. Kaji, H. Kohno, and S. Zen, Bull. Chem. Soc. Jpn., 50, 928 (1977).
2. A.T. Nielsen, “The Chemistry of the Nitro and Nitroso Groups, ” Part I, ed. by H. Feuer, Interscience Publishers, New York, 1969, pp. 461—468
3. A. McKillop and R.J. Kobylecki, Tetrahedron, 30, 1365 (1974).
4. E. Kaji, A. Igarashi, and S. Zen, Bull. Chem. Soc. Jpn., 49, 3181 (1976)
5. J.V.R. Kaufman and J.P. Picard, Chem. Rev., 59, 429 (1959).
6. T. Mukaiyama and T. Hoshino, J. Am. Chem. Soc. 82, 5339 (1960)
7. G.B. Bachman and L.E. Strom, J. Org. Chem., 28, 1150 (1963)
8. J.E. McMurry, “Organic Syntheses, ” vol. 53, ed. by A. Brossi, John Wiley and Sons, Inc., New York, 1973, p. 59.).
9. C. Musante, Gazz. Chim. Ital., 70, 685 (1940).
10. G. Casnati and A. Ricca, Tetrahedron Lett., 1967, 327.
11. P. Battioni, L. Vo-Quang, J.C. Raymond, and Y. Vo-Quang, C.R. Acad. Sci. Paris (C), t.271, 1468 (1970)
12. J.E. Franz and H.K. Pearl, J.Org. Chem., 41 1296 (1976).
13. G. Labbe and G. Mathys, J.Org. Chem., 39, 1221 (1974).
14. L. Panizzi, Gazz. Chim. Ital., 70, 119 (1940).