Issue 7, 2011

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

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

Supplementary files

Article information

Article type
Paper
Submitted
12 Oct 2010
Accepted
20 Jan 2011
First published
22 Feb 2011

Org. Biomol. Chem., 2011,9, 2535-2538

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

M. Blangetti, A. Deagostino, G. Gervasio, D. Marabello, C. Prandi and P. Venturello, Org. Biomol. Chem., 2011, 9, 2535 DOI: 10.1039/C0OB00867B

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