Syntheses of Thiocarboxamides

Abstract

Methods for the preparation of thiocarboxamides are described with special reference to progress achieved in the last few years. The discussion is arranged according to the eight most important reaction types. Reaction of nitriles with hydrogen sulfide and thiolsReaction of imidic acid derivatives with hydrogen sulfide and thiols Sulfurization of amides Addition of nucleophiles t o isothiocyanates

Structure of 6,13-bis(butylthio)-5,12-dioxa-6,13-dithioxo-6a,7,13a,14-tetraaza-6,13-diphosphadibenz[a,h]anthracene

“…The ortho-difunctional group compounds reacting with PaS 5 to form stable sixmembered phosphacyclic compounds have been reported by Legrand (1968), Walter & Bode (1966) and Sumitomo Chemical Co. Ltd (1980). Many of these compounds have biological activity and some of the crystal structures have been determined by Perales, Fayos & Garcia-Blanco (1979) and GarciaBlanco & Perales (1972).…”

Elemental Sulfur and its Reactions

“…About 39,50,51,52 show that these complex and experimentally quite different reactions cannot be interpreted by just one mechanism alone (e [. refs.…”

Synthesis of Thioamides and Thiolactams

“…1 ,28,29 The approach was successfully employed in the synthesis of thiobenzoyl azolides, e. g. in the formation of (7) according to equation (4).30 However, the compounds are unpleasant to handle and, due to their limited stability, often give only low yields of thioamides in the reaction with amines.…”

“…Consequently, thiocarbonyl compounds are in general highly reactive and have a tendency to di-, oligo-or poly-merize. [4][5][6][7] The most important uses are as synthetic intermediates 5 ,8-10 and in heterocyclic synthesis. 2 In contrast, thioamides (1) are usually perfectly stable and can be handled without problems.…”

“…Using primary aliphatic amines, ring opening of isocoumarin-derived thiolactones (3) according to equation (2) offers a convenient access to o-(2-oxoalkyl)thiobenzamides (4) …”