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Issue 3, 2012
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Application of stable fused dienolates for diversity oriented synthesis of 2,5-dioxo-5,6,7,8-tetrahydro-2H-chromene-3-carboxamides

Maria A. Vodolazhenko,a  Nikolay Yu. Gorobets,*a  Sergey A. Yermolayev,a  Vladimir V. Musatov,a  Valentin A. Chebanov*a  and  Sergey M. Desenkoa 
Author affiliations

* Corresponding authors

a Department of Chemistry of Heterocyclic Compounds, SSI “Institute for Single Crystals” of National Academy of Sciences of Ukraine, Lenin Avenue 60, Kharkiv, Ukraine
E-mail: gorobets@isc.kharkov.com; chebanov@isc.kharkov.com
Fax: +38 (057) 340 9343
Tel: +38 057 341 0256

Abstract

A novel one-pot three-step method for the synthesis of 2,5-dioxo-5,6,7,8-tetrahydro-2H-chromene-3-carboxamide derivatives via hydrolysis of 4-cyanobuta-1,3-dienolate salts was developed. These chromenes contain a 2-pyrone scaffold which is present in many well-known natural and synthetic biologically active compounds. Employing our protocol, a 55 compounds library was quickly generated from 1,3-cyclohexanediones, dimethylformamide dimethylacetal, and various N-substituted cyanacetamides.

Graphical abstract: Application of stable fused dienolates for diversity oriented synthesis of 2,5-dioxo-5,6,7,8-tetrahydro-2H-chromene-3-carboxamides

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Publication details

The article was received on 14 Sep 2011, accepted on 18 Oct 2011 and first published on 02 Dec 2011


Article type: Paper
DOI: 10.1039/C1RA00723H
Citation: RSC Adv., 2012,2, 1106-1111

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    Application of stable fused dienolates for diversity oriented synthesis of 2,5-dioxo-5,6,7,8-tetrahydro-2H-chromene-3-carboxamides

    M. A. Vodolazhenko, N. Yu. Gorobets, S. A. Yermolayev, V. V. Musatov, V. A. Chebanov and S. M. Desenko, RSC Adv., 2012, 2, 1106
    DOI: 10.1039/C1RA00723H

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