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Efficient synthesis of 3‐arylaminopyrroline‐2‐ones by the tandem reaction of anilines and β,γ‐unsaturated α‐ketoesters
Author(s) -
Wu YanChao,
Liu Li,
Wang Dong,
Chen YongJun
Publication year - 2006
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.5570430421
Subject(s) - chemistry , dichloromethane , intramolecular force , boiling , tandem , substrate (aquarium) , condensation , condensation reaction , combinatorial chemistry , aniline , cascade reaction , computational chemistry , organic chemistry , catalysis , materials science , oceanography , physics , solvent , composite material , thermodynamics , geology
A concise and efficient synthetic approach to 3‐arylaminopyrroline‐2‐ones from anilines and β,γ‐unsaturated α‐ketoesters in boiling dichloromethane has been developed. This protocol possesses many advantages such as short reaction time, high isolated yields, and expanding substrate scopes. According to the isolated intermediates and controlled reactions, the reaction was tentatively proposed to involve the Michael addition/condensation and subsequent intramolecular cyclization. The structures of the title compounds were unambiguously confirmed by various spectral data such as X‐ray crystallographic analysis.