Saturated heterocycles. Part 216 . Synthesis, structure and ring opening of trans‐perhydro‐1,4‐benzoxazepin‐3‐one derivatives

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Abstract

trans‐Perhydro‐1,4‐benzoxazepin‐3‐ones 2a‐c were synthesized and transformed to condensed‐skeleton perhydro‐trans‐1,4‐benzoxazepines 3a,b, the thiones 4a,b, the urea derivatives 5a,b, and N‐acylated compounds 6a‐e. Compounds 6b,d were ring‐opened by hydrochloric acid in ethanol to yield trans‐2‐(1‐carbethoxyethoxy)‐1‐acylaminomethylcyclohexane derivatives 7b,d. The 1H‐ and 13C‐nmr investigation and X‐ray analysis of 5b and 6c,d proved that the expected N‐acylated derivatives were formed and that both rings of the trans anellated compounds have a chair conformation.

Original languageEnglish
Pages (from-to)161-167
Number of pages7
JournalJournal of Heterocyclic Chemistry
Volume32
Issue number1
DOIs
Publication statusPublished - Jan 1 1995

ASJC Scopus subject areas

  • Organic Chemistry

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