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

ABSTRACT: 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 ?-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.

SUBMITTER: Thimmarayaperumal S

PROVIDER: S-EPMC6641896 | biostudies-literature | 2017 Aug

REPOSITORIES: biostudies-literature

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Base-Promoted Selective Synthesis of 2<i>H</i>-Pyranones and Tetrahydronaphthalenes via Domino Reactions.

Thimmarayaperumal Solaimalai S Shanmugam Sivakumar S

ACS omega 20170824 8

A highly efficient domino protocol has been developed for the synthesis of 6-aryl-4-(methylthio/amine-1-yl)-2-oxo-2<i>H</i>-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 ...[more]

PMID: 31457769

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