Reaktionen mit N-Acylimino-dithiokohlensäurediestern

✍ Scribed by Prof. Dr. M. Augustin; Dr. M. Richter; S. Salas

• Book ID: 105352098
• Publisher: John Wiley and Sons
• Year: 1980
• Tongue: English
• Weight: 579 KB
• Volume: 322
• Category: Article
• ISSN: 1615-4150
• DOI: 10.1002/prac.19803220109

✦ Synopsis

Reactions with N‐Acylimino‐dithiocarbonic‐acid‐diesters.

Reactions of N‐acylimino‐dithiocarbonic‐acid‐S,S‐diesters 1 with nucleophilic com‐pounds present new possibilities to synthesize heterocycles. With amines 1a reacts by mono‐ and disubstitution, respectively, of methylthio‐groups to isothioureas 2 and guanidines 3, with 1,2‐bi‐nucleophilic arenes to benzoheterocycles 4, with aliphatic diamines to imidazolidines 5, pyrimidines 6, diazepines 7 and the hexamethylene‐diamine‐derivatives 8. 1a reacts also with hydrazines to 1,2,4‐triazoles 9 and with hydrazides to the thiosemicarbazones 10 or 1,3,4‐oxadiazoles 11. Heterocyclisations of 1 with guanidines, thiourea, salts of thiourea and amidines give the 1,3,5‐triazines 12, 14, 15 and 16. N‐benzoyl‐dithiocarbonic‐acid‐methylester ‐amid reacts with CH‐acidic compounds to thiazoles 17. The structures of the final products are determined by i.r.‐, ^1^H‐n.m.r.‐, u.v.‐ and mass‐spectras.