Premium
Synthesis, stereochemistry and pharmacological activity of rac.‐ cis ‐tetrahydro‐6‐hydroxy‐7‐(4‐methoxyphenyl)‐1,4‐thiazepin‐5(2 H )‐ones
Author(s) -
Mohacsi Erno,
O'Brien Jay P.,
Todaro Louis J.
Publication year - 1992
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.5570290135
Subject(s) - chemistry , stereochemistry , ring (chemistry) , blocking (statistics) , solid state , product (mathematics) , organic chemistry , statistics , mathematics , geometry
Reaction of 2‐aminoethanethiol ( 3 ) with trans ‐3‐( p ‐methoxyplienyl)glycidate ( 4 ) gave the rac.‐ cis ‐1,4‐thiazepinone 5 and a by‐product 6 . The structure of 5 was proven by X‐ray crystallography. The X‐ray data revealed that this compound adopts the chair conformation in the solid state and the heterocyclic ring is sevenmembered. The structure of the by‐product 6 was elucidated on the basis of spectral data. Compounds 9 and 10 were inactive as calcium channel blocking agents.