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Chemoselective synthesis of m-teraryls through ring transformation of 2H-pyran-2-ones by 2-(1-arylethylidene)-malononitriles

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Abstract

We have developed a simple, efficient and chemoselective approach for the synthesis of m-teraryls by the reaction of 6-aryl-2-oxo-4-(sec.amino)-2H-pyran-3-carbonitriles and 2-(1-arylethylidene)malononitriles under basic conditions. We used 6-aryl-2-oxo-4-methylsulfanyl-2H-pyran-3-carbonitriles as precursors and successfully afforded 5′-methylsulfanyl-[1,1′;3′,1′′]teraryl-4′-carbonitriles. We tried to understand the difference in the reactivity of structurally symmetrical molecules, such as allyl cyanide, 2-cyanomethylbenzonitrile and 2-(1-arylethylidene)malononitrile. The structure of 4′′-methyl-5′-(piperidin-1-yl)-[1,1′:3′,1′′-terphenyl]-4′-carbonitrile was confirmed by single crystal X-ray diffraction analysis.

Graphical abstract: Chemoselective synthesis of m-teraryls through ring transformation of 2H-pyran-2-ones by 2-(1-arylethylidene)-malononitriles

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Publication details

The article was received on 23 Sep 2018, accepted on 31 Oct 2018 and first published on 31 Oct 2018


Article type: Paper
DOI: 10.1039/C8OB02370K
Citation: Org. Biomol. Chem., 2018, Advance Article
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    Chemoselective synthesis of m-teraryls through ring transformation of 2H-pyran-2-ones by 2-(1-arylethylidene)-malononitriles

    R. Panwar, Shally, R. Shaw, A. Elagamy and R. Pratap, Org. Biomol. Chem., 2018, Advance Article , DOI: 10.1039/C8OB02370K

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