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Studies on the chemistry of 2,3,5,6‐tetrahydro‐6‐phenylimidazo[2,1‐ b ]‐thiazole II. Reaction with nucleophiles
Author(s) -
Bigg D. C. H.,
Purvis S. R.
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.5570140414
Subject(s) - chemistry , nucleophile , electrophile , thiazole , pyrrolidine , medicinal chemistry , thio , carbon atom , ring (chemistry) , stereochemistry , organic chemistry , catalysis
The title compound behaves as an ambident electrophile which reacts with alkylthiols, thio‐phenols, and sodium diethyldithiocarbamate to give 1‐(2‐substituted ethyl)‐4‐phenylimidazolidine‐2‐thiones by attack at C‐2. In contrast, the reaction with pyrrolidine involves attack at the bridgehead carbon atom, followed by elimination of thiirane, to give 4‐phenyl‐2‐(1‐pyrrolidino)‐imidazoline.