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Research on heterocyclic compounds. XX. Synthesis of trifluoromethyl derivatives of fused imidazole systems
Author(s) -
Abignente Enrico,
de Caprariis Paolo,
Patscot Rosaria,
Sacchi Antonella
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.5570230413
Subject(s) - chemistry , imidazole , trifluoromethyl , moiety , pyridinium , ring (chemistry) , pyridine , nitrogen atom , medicinal chemistry , bromide , stereochemistry , organic chemistry , alkyl
A series of heterocyclic compounds having an imidazole ring fused with another ring with a bridgehead nitrogen atom and bearing a trifluoromethyl moiety was synthesized by reaction of 3‐bromo‐1,1,1‐trifluoroacetone with various heteroarylamines. In some cases, an intermediate compound obtained together with the required product was isolated and its structure was elucidated: e.g. , starting from 2‐aminopyridine we have obtained 2‐trifluoromethylimidazo[1,2‐a]pyridine and 2‐hydroxy‐2‐trifluoromethyl‐2,3‐dihydro‐1 H ‐imidazo [1,2‐ a ]pyridinium bromide. Such results confirmed the mechanism previously proposed for this reaction.