A convenient synthesis of symmetrical N,N′-dialkylureas by the reactions of 4-chloro-5H-1,2,3-dithiazol-5-one with alkylamines

The Reaction of DABCO with 4-Chloro-5H-1,2,3-dithiazoles: Synthesis and Chemistry of 4-[N-(2-Chloroethyl)piperazin-1-yl]-5H-1,2,3-dithiazoles

“…Carbimidoyl cyanides, analogous to 17 , were observed previously by Kim et al, , in the reaction of 1,2,3-dithiazoles 2a – c with dialkylamines, and a mechanistic rationale was provided. A similar mechanism could take place in this case; however, the attacking nucleophile can be either DABCO or free N -(2-chloroethyl)­piperazine ( 21a ), which, as mentioned above, could be present in minor quantities in the reaction mixture.…”

Iodine-DMSO mediated conversion of N-arylcyanothioformamides to N-arylcyanoformamides and the unexpected formation of 2-cyanobenzothiazoles

“…15 Several other earlier reports described the formation of cyanoformamides. 16–21 For instance, hydration of cyanogen under high pressure using excess water gave 1-cyanoformamide, 16 whereas reaction of 5-hydroxyimino-1,3-dioxine-4,6-dione (isonitroso Meldrum's acid) with carbodiimides ( N , N ′-dicyclohexylcarbodiimide and N , N ′-diisopropylcarbodiimide) gave N -cyclohexylcyanoformamide and N -isopropylcyanoformamide, respectively. 17 Some other reagents like tetracyanoethylene, 18 5-tosyloxyimino-2,2-dimethyl-1,3-dioxane-4,6-dione, 19 4-chloro-5 H -1,2,3-dithiazol-5-one, 20 tetraalkyl-cyanoformamidinium salt, 21 or dichlorosulfenyl chlorides 22 have been employed in the synthesis of similar types of synthetic compounds.…”

Synthesis of cyanoformamides from primary amines and carbon dioxide under mild conditions. Synthesis of ceratinamine

“…6 Cyanoformamides have also been proposed as intermediates in the synthesis of symmetrical N,N¢-dialkylureas. 7 Only a few methods have been described in the literature to prepare cyanoformamides from amines. The most simple approaches make use of reagents like carbonyl cyanide 3 (prepared Departamento de Química Orgánica, Facultade de Química, Universidade de Vigo, 36310 Vigo, Spain.…”