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The oxidative cyclization of n ‐phenyl‐3‐methylthiopropylamines to form N ‐phenyl‐s‐methylisothiazolidinium salts
Author(s) -
Swank Darrell W.,
Lambeth David O.
Publication year - 1983
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.5570200655
Subject(s) - chemistry , succinimide , sodium cyanoborohydride , tetraphenylborate , sodium tetraphenylborate , sodium salt , medicinal chemistry , salt (chemistry) , organic chemistry , ion , inorganic chemistry
A series of N ‐phenyl‐3‐methylthiopropylamine hydrochlorides were prepared by reacting a series of anilines with methional and sodium cyanoborohydride. These were cyclized upon oxidation by N ‐chloro‐succinimide to the corresponding N ‐phenyl‐S‐methylisothiazolidinium derivatives which were isolated as the tetraphenylborate salts. Compounds successfully prepared included the m ‐methyl, p ‐methyl, m ‐methoxy, and p ‐methoxyphenyl derivatives.