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Abstract
Pyridine dicarbonitriles have been synthesized in good yields via a one-pot multi–component reaction of aldehyde, malononitrile, and thiol in the presence of nano-TiO2 as a catalyst in ethanol. KEY WORDS: Pyridine dicarbonitriles, Multi–component reaction, One-pot, Nano-TiO2 Bull. Chem. Soc. Ethiop. 2014, 28(1), 149-153.DOI: http://dx.doi.org/10.4314/bcse.v28i1.18
Highlights
Multicomponent reactions (MCRs) have become important tools in modern preparative synthetic chemistry because these reactions increase the efficiency by combining several operational steps without any isolation of intermediates or change of the conditions [1, 2] and multicomponent reactions (MCRs) have recently emerged as valuable tools in the preparation of structurally diverse chemical libraries of drug-like heterocyclic compounds [3,4,5]
The synthesis of highly substituted pyridines has attracted much attention, and a number of procedures have been developed using a variety of protocols, such as hetero-Diels-Alder reaction of 3-siloxy-1-aza1,3-butadienes with electron-deficient acetylenes [8], three-component condensation of aldehyde, malononitrile, and thiol [9], ruthenium-catalyzed cycloisomerization of 3-azadienynes [10], Mannich reaction of aldehydes and iminium salts [11] and Vilsmeier-Haack reaction of Rhydroxyketenedithioacetals [12]
One of the very convenient approaches which attracted our attention is the three-component condensation of aldehyde, malononitrile, and thiol to the highly substituted pyridines developed by Evdokimov et al [9]
Summary
Multicomponent reactions (MCRs) have become important tools in modern preparative synthetic chemistry because these reactions increase the efficiency by combining several operational steps without any isolation of intermediates or change of the conditions [1, 2] and MCRs have recently emerged as valuable tools in the preparation of structurally diverse chemical libraries of drug-like heterocyclic compounds [3,4,5]. The synthesis of highly substituted pyridines has attracted much attention, and a number of procedures have been developed using a variety of protocols, such as hetero-Diels-Alder reaction of 3-siloxy-1-aza1,3-butadienes with electron-deficient acetylenes [8], three-component condensation of aldehyde, malononitrile, and thiol [9], ruthenium-catalyzed cycloisomerization of 3-azadienynes [10], Mannich reaction of aldehydes and iminium salts [11] and Vilsmeier-Haack reaction of Rhydroxyketenedithioacetals [12]. One of the very convenient approaches which attracted our attention is the three-component condensation of aldehyde, malononitrile, and thiol to the highly substituted pyridines developed by Evdokimov et al [9]. We report a mild, practical and highly efficient procedure for the preparation of the title compounds using nanoTiO2 catalyst at room temperature (Scheme 1).
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