A Rich Array of Reactions of Cyanomonothiocarbonylmalonamides RNHCSCH(CN)CONHR‘ and Their Thioenols RNHC(SH)C(CN)CONHR‘¹

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.由氰单硫代羰基丙二酰胺类（cyanomonothiocarbonylmalonamides）与氰二硫代羰基丙二酰胺（cyanodithiocarbonylmalonamide）衍生得到的硫烯醇（thioenol）被证实为具有高反应活性的物种。该类硫烯醇可在多种条件下发生反应，包括结晶过程、与多种羰基化合物的反应，以及与另一分子硫烯醇的反应，最终生成多种产物，其中以杂环化合物为主，具体包括取代型2,3-二氢异噻唑-3-酮及其3-硫酮、2-取代亚甲基噻唑、3,4-二氢-1,3-噻嗪-4-酮及其4-硫酮、二乙烯基硫醚、1,2-二硫环戊烷自由基，以及3,7-二氮杂双环[3.3.0]辛烷衍生物。针对这些反应所提出的反应机理包括自由基机理、亲核取代反应以及缩合反应。