1,2‐Benzothiazines VIII.  A novel semmler‐wolff type transformation of 2‐methyl‐2H‐1,2‐benzothiazin‐4 ‐one 1,1‐dioxide oxime | Zendy

Zinnes Harold | Zendy; Comes Roger A. | Zendy; Shavel John | Zendy

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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.

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