Reaction of 3H, 6H‐1, 2‐Dithiolo[4,3‐c]1,2‐dithiole‐3, 6‐dithione with primary aliphatic amines

Abstract

The reaction of 3H,6H‐1,2‐dithiolo[4,3‐c]1,2‐dithiole‐3, 6‐dithione (1) with primary aliphatic amines (8a,b) gives 3H,6H‐3,6‐bisalkylimino‐1,2‐dithiolo[4,3‐c]1,2‐ dithiole (9a,b), 3H,3‐N‐alkylamino‐5‐N‐alkylthiocarbamido‐1, 2‐dithiolium‐4‐thiolate (10a,b) and 3H,3‐N‐alkylimino‐4‐alkylamino‐5‐N‐alkylthiocarbamido‐1,2‐dithiole (11a,b). The compounds 9‐11 can be formed from one another. The compounds 10a,b react with nickel chloride to the stable complexes 14a,b. In basic medium 10 gives the salt of 3H,3N‐alkylthiocarbamido‐1,2‐dithiole‐4‐thiolate 15, which reacts with methyl iodide to 3H,3N‐alkylimino‐5‐N‐alkylthiocarbamido‐4‐methylthio‐1,2‐dithiole 16.

Reaction of substituted 1-methylthio-4,5-dihydro[1,2]dithiolo[3,4-c]quinolin iodides with arylamines. Synthesis of novel 1,2-dithiolo[3,4-c]quinolin-1-ylidene(aryl)amines and 10-(arylimino)-7,10-dihydro[1,2]dithiolo[3,4-c]pyrrolo[3,2,1-ij]quinoline-4,5-diones

“…[1][2][3][4][5][6][7][8][9][10] Basically, the reaction with primary aliphatic and aromatic amines tends not to be selective and leads to a mixture of 1,2-dithiol-3-imines and 1,2-thiazol-3-thiones, which exist in the "dynamic isomerism" due to transformation by Dimroth-type rearrangement. [11][12][13][14][15][16] Although we did not find any information about reactions of 4,5-dihydro-4,4-dimethyl-1H-1,2-dithiolo [3,4-c]quinoline-1-thiones 1 with amines, the reaction of their methylthio-dithiolium salts 2 with arylamines has been described earlier. 17 According to the author, the salts 2a,b reacted with p-phenetidine in boiling ethanol with loss of a methyl mercaptan molecule to form a substituted 1,2-dithiol-3-imines 3a,b.…”