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

Overview

Journal ACS Omega

Publisher American Chemical Society

Specialty Chemistry

Date 2019 Aug 29

PMID 31457769

Citations 2

Authors

Solaimalai Thimmarayaperumal

Sivakumar Shanmugam

Affiliations

Soon will be listed here.

Abstract

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

Citing Articles

Emission solvatochromic, solid-state and aggregation-induced emissive α-pyrones and emission-tuneable 1-pyridines by Michael addition-cyclocondensation sequences.

Breuer N, Gruber I, Janiak C, Muller T Beilstein J Org Chem. 2019; 15:2684-2703.

PMID: 31807204 PMC: 6880829. DOI: 10.3762/bjoc.15.262.

Metal-Free Vinyl C-H Sulfenylation/Alkyl Thiolation of Ketene Dithioacetals for the Synthesis of Polythiolated Alkenes.

Deng L, Liu Y ACS Omega. 2019; 3(9):11890-11895.

PMID: 31459275 PMC: 6645039. DOI: 10.1021/acsomega.8b01946.

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