Premium
Intramolecular sulphonamidomethylation. Part II . Fused heterocycles from 2‐phenylethanesulphonamides
Author(s) -
Zinczuk Juan,
Sorokin Isidoro H.,
Orazi Orfeo O.,
Corral Renée A.
Publication year - 1992
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.5570290432
Subject(s) - chemistry , substituent , ring (chemistry) , nitrogen atom , intramolecular force , carbon atom , medicinal chemistry , stereochemistry , closure (psychology) , group (periodic table) , nitrogen , organic chemistry , economics , market economy
1,2,4,5‐Tetrahydro‐3,2‐benzothiazepine 3,3‐dioxides 2 , with a variety of substituents on the nitrogen atom, can be easily obtained by the title reaction. The isomeric compounds 4–6 are also formed from sulphonamides bearing an N ‐aralkyl group with a chain of two or more carbon atoms. Activation of the ring closure‐position or deactivation of the aromatic ring in the substituent can direct the reaction to give compounds 2 . Cyclization results are influenced by the size of the new heterocycle ring and by the predominant formation of derivatives with the SO 2 group outside the ring.