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

Solaimalai Thimmarayaperumal | Zendy; Sivakumar Shanmugam | Zendy

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

Author(s) -

Solaimalai Thimmarayaperumal,

Sivakumar Shanmugam

Publication year - 2017

Publication title -

acs omega

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.779

H-Index - 40

ISSN - 2470-1343

DOI - 10.1021/acsomega.7b00627

Subject(s) - domino , malononitrile , chemistry , cyclohexanone , amine gas treating , pyran , intramolecular force , aryl , combinatorial chemistry , cascade reaction , organic chemistry , catalysis , alkyl

A highly efficient domino protocol has been developed for the synthesis of 6-aryl-4-(methylthio/amine-1-yl)-2-oxo-2 H -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-2 H -pyran-3-carbonitrile plays multiple roles in the construction of various novel polyaromatic hydrocarbons.

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