Reaction of Bromoenones with Amidines: A Simple Catalyst-Free Approach to Trifluoromethylated Pyrimidines

Abstract A facile one-pot synthesis of trifluoromethylated pyrimidines has been achieved by the treatment of fluorinated 2-bromoenones with aryl- and alkylamidines. The assembly of pyrimidine core proceeds by the cascade reactions via aza-Michael addition–intramolecular cyclization–dehydrohalogenati...

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Bibliographic Details
Published in:Synthesis (Stuttgart) 2020-05, Vol.52 (10), p.1512-1522
Main Authors: Romanov, Alexey R., Rulev, Alexander Yu, Popov, Alexander V., Kondrashov, Evgeniy V., Zinchenko, Sergey V.
Format: Article
Language:English
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Summary:Abstract A facile one-pot synthesis of trifluoromethylated pyrimidines has been achieved by the treatment of fluorinated 2-bromoenones with aryl- and alkylamidines. The assembly of pyrimidine core proceeds by the cascade reactions via aza-Michael addition–intramolecular cyclization–dehydrohalogenation/dehydration sequence. This strategy is featured by high selectivity and mild reaction conditions giving the target heterocycles in high yields (up to 99%). The unique influence of trifluoromethyl group on the reaction path is demonstrated.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0040-1707969