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Issue 8, 2020
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A [bmim]Cl-promoted domino protocol using an isocyanide-based [4+1]-cycloaddition reaction for the synthesis of diversely functionalized 3-alkylamino-2-alkyl/aryl/hetero-aryl indolizine-1-carbonitriles under solvent-free conditions

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Abstract

A domino protocol involving aldehydes, isocyanides and 2-pyridylacetonitrile in the presence of [bmim]Cl as a promoter and solvent for the synthesis of 3-alkylamino-2-alkyl/arylindolizine-1-carbonitriles is described. A wide range of alkyl, aryl and hetero-aryl aldehydes reacted with 2-pyridylacetonitrile and isocyanides, leading to indolizine derivatives with high selectivity, high atom economy, and good to excellent yields. This straight-forward and highly efficient method allows the synthesis of bis-indolizine-1-carbonitrile derivatives.

Graphical abstract: A [bmim]Cl-promoted domino protocol using an isocyanide-based [4+1]-cycloaddition reaction for the synthesis of diversely functionalized 3-alkylamino-2-alkyl/aryl/hetero-aryl indolizine-1-carbonitriles under solvent-free conditions

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Article information


Submitted
18 Nov 2019
Accepted
17 Jan 2020
First published
21 Jan 2020

New J. Chem., 2020,44, 3241-3248
Article type
Paper

A [bmim]Cl-promoted domino protocol using an isocyanide-based [4+1]-cycloaddition reaction for the synthesis of diversely functionalized 3-alkylamino-2-alkyl/aryl/hetero-aryl indolizine-1-carbonitriles under solvent-free conditions

A. B. Atar, J. Kang and A. H. Jadhav, New J. Chem., 2020, 44, 3241
DOI: 10.1039/C9NJ05738B

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