Base-Promoted Selective Synthesis of 2H‑Pyranones and Tetrahydronaphthalenes via Domino Reactions

A highly efficient domino protocol has been developed for the synthesis of 6-aryl-4-(methylthio/amine-1-yl)-2-oxo-2H-pyran-3-carbonitriles and 4-aryl-2-(amine-1-yl)-5,6,7,8-tetrahydronaphthalene-1-carbonitriles from simple and readily available α-aroylketene dithioacetals, malononitrile, secondary a...

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Published inACS omega Vol. 2; no. 8; pp. 4900 - 4910
Main Authors Thimmarayaperumal, Solaimalai, Shanmugam, Sivakumar
Format Journal Article
LanguageEnglish
Published American Chemical Society 31.08.2017
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Summary:A highly efficient domino protocol has been developed for the synthesis of 6-aryl-4-(methylthio/amine-1-yl)-2-oxo-2H-pyran-3-carbonitriles and 4-aryl-2-(amine-1-yl)-5,6,7,8-tetrahydronaphthalene-1-carbonitriles from simple and readily available α-aroylketene dithioacetals, malononitrile, secondary amines, and cyclohexanone. This elegant domino process involved consecutive addition–elimination, intramolecular cyclization, and ring opening and closing sequences. Notably, in situ generated 2-imino-4-(methylthio/amine-1-yl)-6-aryl-2H-pyran-3-carbonitrile plays multiple roles in the construction of various novel polyaromatic hydrocarbons.
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ISSN:2470-1343
2470-1343
DOI:10.1021/acsomega.7b00627