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

Org Biomol Chem. 2018 Nov 28;16(46):8994-9002. doi: 10.1039/c8ob02370k.

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.

Publication types

  • Research Support, Non-U.S. Gov't