Metal-free synthesis of cyclic di-oxoguanidines via one-pot sequential transformation of amines, carbodiimides and acyl dichlorides.
The one-pot sequential reaction of various amines, carbodiimides, and acyl dichlorides has been achieved for the first time under metal-free conditions to provide symmetric cyclic di-oxoguanidines via an unexpected 2,2-dichloro-imidazolidindione intermediate. Acyl dichlorides have a dual function: to serve as the third component and to activate carbodiimides. In sharp contrast, the AlMe(3)-catalyzed sequential reaction from the same substrates gives the isomer.
Beijing National Laboratory for Molecular Science (BNLMS), College of Chemistry, Peking University, Beijing 100871, China.
Fei
F
Zhao
Yang
Y
Wang
Wen-Xiong
WX
Zhang
Zhenfeng
Z
Xi
D000588:Amines / Q000737:chemistry*; D002234:Carbodiimides / Q000737:chemistry*; D002384:Catalysis; D002712:Chlorides / Q000737:chemistry*; D003500:Cyclization; D006146:Guanidines / Q000138:chemical synthesis* / Q000737:chemistry; D010100:Oxygen / Q000737:chemistry*
D000588:Amines; D002234:Carbodiimides; D002712:Chlorides; D006146:Guanidines; D010100:Oxygen