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A base induced fragmentation of tetramisole
Author(s) -
Fibiger Richard F.,
Banks Allen R.,
Jones Ted,
Haltiwanger R. Curtis,
Watt David S.
Publication year - 1978
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.5570150225
Subject(s) - lithium diisopropylamide , chemistry , tetrahydrofuran , thiazole , halide , alkyl , ring (chemistry) , fragmentation (computing) , lithium (medication) , medicinal chemistry , crystal structure , isopropyl , stereochemistry , organic chemistry , ion , deprotonation , solvent , medicine , computer science , endocrinology , operating system
The exposure of dl ‐2,3,5,6‐tetrahydro‐6‐phenylimidazo[2,1‐6 Jthiazole (tetramisole) to lithium diisopropylamide in tetrahydrofuran ruptures the thiazole ring to give, following the introduction of primary or secondary alkyl halides, 1‐(2′‐alkylthio)ethyl‐4‐phenylimidazoles. Conclusive evidence for the thiazole ring opening was obtained by a single crystal x‐ray diffraction study of 1‐(2′‐ p ‐bromobenzylthio)ethyl‐4‐phenylimidazole.