Reaction of chromones with hydroxylamine in anhydrous methanol. A novel route for the preparation of chromone oximes

Vince Szabó, János Borbély, Edit Theisz, Sándor Nagy

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

The reaction of 4H-1-benzopyran-4-one (chromone, bar1,) and its substituted derivatives with hydroxylamine in aqueous alcohols gives isoxazoles 5 and 10, as the major products, whereas 1a is transformed mainly into 8a with hydroxylamine hydrochloride in anhydrous methanol, compounds 5a, 9a and 10a can be also isolated, and the formation of 6a and 7a has been detected, as well. Depending on the character of the substituent, substituted chromones 1b-g afforded 7,8 or 9 as the isolable major product. Based on the present experiments compound 6, produced in an acid-catalyzed methanol addition on 1, is regarded the key intermediate of the formation of chromone oxime.

Original languageEnglish
Pages (from-to)4215-4222
Number of pages8
JournalTetrahedron
Volume42
Issue number15
DOIs
Publication statusPublished - 1986

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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