Structures of saturated azeto[1,2-a][3,1]- and azeto-[2,1-b][1,3]benzoxazines prepared by addition of chloroacetyl chlorides to cyclohexane-condensed dihydrooxazines

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5 Citations (Scopus)

Abstract

Saturated cis and trans 3,1- and 1,3-benzoxazines (1-4) reacted with chloroacetyl chlorides to yield azeto[1,2-a][3,1]- and [2,1-b][1,3]benzoxazines (5, 6, 8, 9a,b). In one case, the addition took place with partial cis→trans inversion of the starting compound. Adduct (7), containing two condensed 1,3-oxazine rings, was also isolated. The stereostructures of the new compounds were proved by 1H- and 13C-nmr spectroscopy, with NOE measurement data. The reaction mechanism is discussed.

Original languageEnglish
Pages (from-to)995-1003
Number of pages9
JournalHeterocycles
Volume36
Issue number5
DOIs
Publication statusPublished - máj. 1 1993

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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