Synthesis of 2-trifluoromethylated quinolines from CF3-alkenes

Autor:	Valentine G. Nenajdenko, Zoia A. Sizova, Vasiliy M. Muzalevskiy, Vladimir T. Abaev
Rok vydání:	2021
Předmět:	chemistry.chemical_compound Chemistry Yield (chemistry) Organic Chemistry Intramolecular cyclization Physical and Theoretical Chemistry Biochemistry Combinatorial chemistry Pyrrolidine
Zdroj:	Organic & Biomolecular Chemistry. 19:4303-4319
ISSN:	1477-0539 1477-0520
Popis:	α-CF3-enamines can be prepared by the reaction of pyrrolidine with the corresponding haloalkenes. The prepared enamines react with 2-nitrobenzaldehydes to give ortho-nitro-substituted α,β-diaryl-CF3-enones highly stereoselectively in up to 88% yield. Subsequent reduction of the nitro-group by an Fe–AcOH system promotes intramolecular cyclization to afford 2-CF3-3-arylquinolines in up to 99% isolated yield. High synthetic utility of all synthetic steps of the sequence was shown. A one-pot procedure was developed to give the target trifluoromethylated quinolines directly from enamines or haloalkenes.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::03b088026f08d0e764d811b3df721457 https://doi.org/10.1039/d1ob00098e Zobrazit plný text záznamu