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Intramolecular sulphonyl‐amidomethylation. Part I . Cyclization of benzylsulphonamides
Author(s) -
Orazi Orfeo O.,
Corral Renée A.,
Bravo Rodolfo
Publication year - 1986
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.5570230620
Subject(s) - chemistry , iminium , imine , intramolecular force , benzothiazine , medicinal chemistry , organic chemistry , catalysis
Cyclization of benzylsulphonamides with aldehydes in strong acid media is a synthetically useful route to 3,4‐dihydro‐1 H ‐2,3‐benzothiazine 2,2‐dioxides III. With insufficient acid strength or reaction time, kinetic products IV and VI are obtained; the latter compounds can be converted into the thermodynamic products III under stronger conditions. The reactions proceed via imine VII or iminium VIII compounds as common intermediates.