A rich array of reactions of Cyanomonothiocarbonylmalonamides RNHCSCH(CN)CONHR' and their Thioenols RNHC(SH)=C(CN)CONHR'1

The Journal of Organic Chemistry
Ahmad Basheer, Zvi Rappoport

Abstract

The thioenols derived from cyanomonothiocarbonylmalonamides and a cyanodithiocarbonylmalonamide were found to be very reactive species. They react under a variety of conditions such as crystallization, reaction with several carbonyl compounds, and reactions with another thioenol molecule to give a variety of products, mostly heterocycles, including substituted 2,3-dihydroisothiazole-3-ones and 3-thione, 2-substituted methylenethiazoles, 3,4-dihydro-1,3-thiazine-4-ones and 4-thiones, divinyl sulfides, a 1,2-dithiolane radical, and a 3,7-diaza[3.3.0]bicyclooctane derivative. Mechanisms suggested for these reactions include radical mechanisms, nucleophilic substitutions, and condensations.

References

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Dec 15, 2006·Organic Letters·Ahmad Basheer, Zvi Rappoport
Jun 15, 2007·The Journal of Organic Chemistry·Ahmad BasheerZvi Rappoport
Sep 1, 2007·The Journal of Organic Chemistry·Jinhua SongZvi Rappoport
Dec 13, 2007·The Journal of Organic Chemistry·Ahmad Basheer, Zvi Rappoport

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Citations

Feb 5, 2015·The Journal of Organic Chemistry·Natalie Margraf, Georg Manolikakes
Apr 5, 2014·The Journal of Organic Chemistry·Thomas KlattPaul Knochel
Sep 30, 2015·The Journal of Organic Chemistry·Lian-Yan LiaoXin-Fang Duan
Nov 24, 2011·The Journal of Organic Chemistry·Regadia AissaouiJacques Mortier
Mar 31, 2015·Chemistry : a European Journal·Raphaël RochatKazushi Mashima
Nov 3, 2016·Chemistry : a European Journal·Kamran T Mahmudov, Armando J L Pombeiro

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