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Issue 21, 2020
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Blaise reaction: synthesis, skeletal diversification of C(4) substituted 5-ylidenepyrrol-(5H)-ones and the role of the strategically located ester on the reactivity of the nitriles

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Abstract

We have achieved a simple and convenient synthesis of several C(4) substituted 5-ylidenepyrrol-(5H)-ones from 3-aryl/heteroaryl/alkyl 3-cyanopropionates and ethyl/methyl bromoacetates via a useful variation of the classical Blaise reaction. The products were further transformed to useful small organic molecules (SOMs). Studies on the reactivity of nitriles via intra and inter-molecular competition experiments showed that anchimeric assistance from the neighbouring and strategically located ester is crucial for higher reactivity of the nitrile in the 3-cyanopropionates towards the Blaise reaction.

Graphical abstract: Blaise reaction: synthesis, skeletal diversification of C(4) substituted 5-ylidenepyrrol-(5H)-ones and the role of the strategically located ester on the reactivity of the nitriles

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Article information


Submitted
14 Jan 2020
Accepted
16 Mar 2020
First published
02 Apr 2020

New J. Chem., 2020,44, 9010-9017
Article type
Paper

Blaise reaction: synthesis, skeletal diversification of C(4) substituted 5-ylidenepyrrol-(5H)-ones and the role of the strategically located ester on the reactivity of the nitriles

H. Surya Prakash Rao and A. H. Padder, New J. Chem., 2020, 44, 9010
DOI: 10.1039/D0NJ00231C

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