Synthesis and dimethyldioxirane oxidation of tetrahydrobenzofurans

Albert Lévai, Marijan Kočevar, Gábor Tóth, András Simon, Lidija Vraničar, Waldemar Adam

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Abstract

On treatment with alkaline hydrogen peroxide (Weitz-Scheffer oxidation), the N-(5,6,7,8-tetrahydro-2,5-di- oxo-2H-1-benzopyran-3-yl)benzamides la-c afforded the N- (4-oxo-4,5,6,7-tetrahydro-1-benzofuran-2-yl)benzamides 2a-c in an unprecedented transformation. These hitherto unknown tetrahydrobenzofuran derivatives have been converted into 2-hydroxy-2-(4-oxo-2-phenyl-4,5-dihydro-1,3-ox- azol-5-yl)cyclohexane-1,3-diones 3a-c by dimethyldioxirane oxidation. Proposed mechanisms for the formation of the furans 2a-c and the 2-hydroxycyclohexane-1,3-diones 3a-c are offered. Structure elucidation of all new compounds has been performed by NMR spectroscopy.

Original languageEnglish
Pages (from-to)1830-1833
Number of pages4
JournalEuropean Journal of Organic Chemistry
Issue number11
DOIs
Publication statusPublished - Jan 1 2002

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Keywords

  • NMR spectroscopy
  • Oxidative transformations
  • Tetrahydrobenzofurans
  • Tetrahydrocoumarins

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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