[Saturated heterocyclic compounds. 216 (1). Synthesis, structure and ring opening of trans-perhydro-1,4-benzoxazepin-3-one derivatives]

Abstract

trans-Perhydro-1,4-benzoxazepin-3-ones 2a-e 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 hydrochloride acid in ethanol to yield trans-2 (1-carbethoxyethoxy)-1-(acylaminomethyl)-cyclohexane 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 annolated compounds have a chair conformation.