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Modulating the Reactivity of α‐Isocyanoacetates: Multicomponent Synthesis of 5‐Methoxyoxazoles and Furopyrrolones
Author(s) -
Bonne Damien,
Dekhane Mouloud,
Zhu Jieping
Publication year - 2007
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200605005
Subject(s) - reactivity (psychology) , nucleophile , aryl , conjugate , component (thermodynamics) , alkyl , chemistry , base (topology) , combinatorial chemistry , organic chemistry , catalysis , mathematics , physics , medicine , mathematical analysis , alternative medicine , pathology , thermodynamics
A simple approach to complexity : The reactivity pattern of α‐isocyanoacetates can be tuned by modulating the acidity of the α CH bond(s) against the nucleophilicity of the conjugate base. The unique reactivity of the α‐( p ‐nitrophenyl)‐α‐isocyanoacetate 1 was exploited in a three‐component synthesis of 5‐methoxyoxazoles 2 and four‐component synthesis of furopyrrolones 3 . R 1 ,R 2 ,R 3 =alkyl, aryl, benzyl; R 4 =aryl.