5-(Arylimino)-4-(dialkylamino)-5H-1,2,3-dithiazoles and the Mechanism of Their Formation

Article abstract of DOI:10.1021/jo00100a018

The reactions of 5-(arylimino)-4-chloro-5H-1,2,3-dithiazoles 1 with excess (6 equiv) bulky dialkylamines such as diethyl-, di-n-propyl-, and di-n-butylamines in CH2Cl2 at room temperature gave 5-(arylimino)-4-(dialkylamino)-5H-1,2,3-dithiazoles 5 in 18-76percent yields.Compounds 5 are formed via (arylimino)cyanomethyl alkylamino disulfides 3.Nucleophilic addition of the amines to the carbon atom of the cyano group of 3 and subsequent cyclization afford 5.