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Superbase promoted synthesis of dienamides as useful intermediates for the synthesis of α-ketoamides, γ-lactams and cyclic imino ethers†
Marco Blangetti,Annamaria Deagostino,Giuliana Gervasio,Domenica Marabello,Cristina Prandi,Paolo Venturello
Organic & Biomolecular Chemistry Pub Date : 02/22/2011 00:00:00 , DOI:10.1039/C0OB00867B
Abstract

Alkoxydienamides 2 have been synthesized exploiting the reactivity of α,β-unsaturated acetals 1 with isocyanates in the presence of Schlosser's superbase LIC–KOR. In a mild acidic medium, 2 can then be promptly converted both into α-ketoamides 3 and into substituted 2-pyrrolidinones 4 or imino ethers 5 by choosing the appropriate experimental conditions.

Graphical abstract: Superbase promoted synthesis of dienamides as useful intermediates for the synthesis of α-ketoamides, γ-lactams and cyclic imino ethers
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