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Studien zur Chemie von O,N‐ und S,N‐haltigen Heterocyclen, 13. Untersuchungen zur Ringverengung von 1,5‐Benzothiazepinen zu 1,4‐Benzothiazinen
Author(s) -
Erker Thomas,
Bartsch Herbert
Publication year - 1992
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.199219920171
Subject(s) - thionyl chloride , chemistry , acetic acid , medicinal chemistry , ring (chemistry) , derivative (finance) , chloride , organic chemistry , financial economics , economics
Studies on the Chemistry of O,N‐ and S,N‐Containing Heterocycles, 13. — Investigations on the Ring Contraction of 1,5‐Benzothiazepines to 1,4‐Benzothiazines Reaction of the (3 R )‐1,5‐benzothiazepinon derivative 5 with NaNO 2 in glacial acetic acid leads to the rac ‐1,4‐benzothiazinone derivatives 6a and 7 . Furthermore, reaction of 5 with NaNO 2 in sulphuric acid/KBr yields the ring‐contracted compound rac ‐ 6b . Compound 8 , after heating with thionyl chloride, affords the E/Z isomeres 9 and 10 .