Synthesis and Rearrangement of 2-Oxo-3-phenylisoxazolo[2,3-α]pyrimidines

Gury Zvilichovsky*, Vadim Gurvich, Shlomo Segev

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

12 Scopus citations

Abstract

2-Oxo-3-phenylisoxazolo[2,3-α]pyrimidine derivatives were synthesized by the reaction of 3-amino-4-phenyl-5-isoxazolone with malonaldehyde tetraacetal, 3-oxobutyraldehyde diacetal, 2,4-pentanedione, and 1-phenyl-1,3-butanedione. The regioselectivity of this reaction was determined by X-ray single crystal structural analysis. Upon heating either in water or in ethanol this bicyclic system underwent a ring opening, followed by decarboxylation to yield phenylpyrimidylmethanol and phenylpyrimidyl methyl ethers. The structures of these 2-oxoisoxazolo[2,3-α]pyrimidines and the mechanism of their rearrangement is discussed.

Original languageEnglish
Pages (from-to)5250-5254
Number of pages5
JournalJournal of Organic Chemistry
Volume60
Issue number16
DOIs
StatePublished - 1 Aug 1995

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