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Variations on the Blaise Reaction: Synthesis of 3,5-Dioxopentanoates and 3-Amino-5-oxopent-3-enoates

H. Surya Prakash Rao*, Nandurka Muthanna

*Department of Chemistry, Pondicherry University, Pondicherry-605 014, India, Email: hspr.chepondiuni.edu.in

H. S. P. Rao, N. Muthanna, Synlett, 2016, 27, 2014-2018.

DOI: 10.1055/s-0035-1561662 (free Supporting Information)


Abstract

A zinc-mediated condensation of readily available α-cyano ketones with ethyl bromoacetate enables a facile and convenient synthesis of various 3,5-diketo esters and 3-amino-5-oxopent-3-enoates. The Blaise reaction on the nitrile occurs in preference to the Reformatsky reaction on the neighboring ketone, possibly due to zinc complexation leading to increased electrophilicity of the nitrile.

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Key Words

Blaise reaction, diketo esters, keto esters, aminooxopentenoates, cyano ketones, ethyl bromoacetate


ID: J60-Y2016