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Issue 23, 2020
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Highly efficient catalyst-free domino conjugate addition, decarboxylation and esterification/amidation of coumarin carboxylic acid/esters with pyrazolones: a green chemistry approach

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Abstract

Tandem conjugate addition, decarboxylation and esterification/amidation of coumarin 3-carboxylic acid derivatives with pyrazolones have been developed. The reactions were performed with coumarin 3-carboxylic acid/esters and pyrazolone in alcohol as a solvent to afford the corresponding pyrazolyl 2-hydroxy phenylpropionate derivatives. Amines and green solvents were employed for amidation in the addition reaction. The methodology has advantages such as excellent yields, a broad substrate scope, catalyst-free, easy purification by simple filtration without any workup, mild conditions and does not require any organic solvents, ligands, base or any additives. This is a green and general synthetic protocol, which could be applicable for the synthesis of substituted pyrazolyl phenyl propionate/amide derivatives. This approach demonstrates the importance of the coumarin 3-carboxylic acid/ester core structure for Michael addition.

Graphical abstract: Highly efficient catalyst-free domino conjugate addition, decarboxylation and esterification/amidation of coumarin carboxylic acid/esters with pyrazolones: a green chemistry approach

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Supplementary files

Article information


Submitted
28 Jan 2020
Accepted
13 Mar 2020
First published
06 Apr 2020

This article is Open Access

RSC Adv., 2020,10, 13866-13871
Article type
Paper

Highly efficient catalyst-free domino conjugate addition, decarboxylation and esterification/amidation of coumarin carboxylic acid/esters with pyrazolones: a green chemistry approach

S. R. Lakshmi, V. Singh and L. R. Chowhan, RSC Adv., 2020, 10, 13866
DOI: 10.1039/D0RA01906B

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