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1,2‐Benzothiazines VIII. A novel semmler‐wolff type transformation of 2‐methyl‐2H‐1,2‐benzothiazin‐4 ‐one 1,1‐dioxide oxime
Author(s) -
Zinnes Harold,
Comes Roger A.,
Shavel John
Publication year - 1977
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.5570140623
Subject(s) - chemistry , boron trifluoride , oxime , derivative (finance) , acetic acid , medicinal chemistry , organic chemistry , catalysis , financial economics , economics
Refluxing the oxime ( 1 ) of 2‐methyl‐2 H ‐1,2‐benzothiazin‐4(3 H )one 1,1‐dioxide with tri‐fluoroacetic acid or with boron trifluoride in acetic acid gives the corresponding N ‐acyl derivative ( 2 or 3) of 4‐amino‐2‐methyl‐2 H ‐1,2‐benzothiazin‐3(4 H )one 1,1‐dioxide. This transformation appears to be related to the acid catalyzed conversion of α‐tetralone oxime to α‐naphthylamine.