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Saturated heterocycles. Part 216 . Synthesis, structure and ring opening of trans ‐perhydro‐1,4‐benzoxazepin‐3‐one derivatives
Author(s) -
Simon Lajos,
Talpas S. Gizella,
Fülöp Ferenc,
Bernáth Gábor,
Argay Gyula,
Kálmán Alajos,
Sohár PÁL
Publication year - 1995
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570320126
Subject(s) - chemistry , ring (chemistry) , yield (engineering) , cyclohexane conformation , hydrochloric acid , stereochemistry , ethanol , organic chemistry , molecule , hydrogen bond , materials science , metallurgy
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 1 H‐ and 13 C‐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.