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Reactivity of 2‐methyl‐4‐(1‐pyrrolidinyl)‐2 H ‐1,2‐benzothiazine 1,1‐dioxide towards p ‐toluenesulphonyl azide
Author(s) -
Consonni Roberto,
Croce Piero Dalla,
Ferraccioli Raffaella
Publication year - 1990
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.5570270260
Subject(s) - chemistry , benzothiazine , azide , enamine , adduct , reactivity (psychology) , nitrogen dioxide , medicinal chemistry , organic chemistry , catalysis , medicine , alternative medicine , pathology
The 2‐methyl‐2 H ‐1,2‐benzothiazin‐4‐(3 H )‐one 1,1 dioxide ( 2 ), obtained according to a new, one‐pot method, is transformed into the pyrrolidino enamine 3 . Reaction of p ‐toluenesulphonyl azide with 3 gives, via an unstable triazoline adduct which loses nitrogen, the two isomeric tosylamino derivatives 4 and 5 . The structures have been assigned by exhaustive nmr analysis and some aspects on their formation and chemical behaviour are discussed.