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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 48, 2018 - Issue 22
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Synthetic Communications Reviews

Synthesis of 2-(3-cyano-5-hydroxy-5-methyl-4-vinylene-1H-pyrrol-2(5H)-ylidene)malononitriles – novel functionalized analogs of tricyanofuran-containing (TCF) push–pull chromophores

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Pages 2850-2858 | Received 26 May 2018, Accepted 10 Jul 2018, Published online: 29 Oct 2018
 

Abstract

2-(3-Cyano-5-hydroxy-4,5-dimethyl-1H-pyrrol-2(5H)-ylidene)malononitrile was synthesized by the interaction between malononitrile dimer and diacetyl. It reacts with aldehydes in ethanol in the presence of ammonium acetate at room temperature and results 2-(3-cyano-5-hydroxy-5-methyl-4-vinylene-1H-pyrrol-2(5H)-ylidene)malononitriles in 66–86% yield. The developed method is of interest as a promising approach to a novel group of push–pull chromophores, which are functionalized analogs of widely used chromophores of the tricyanofuran (TCF) series.GRAPHICAL ABSTRACT

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Funding

This work was supported by Russian Foundation for Basic Research, Grant No. 16-33-60156 mol_a_dk.

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