An efficient direct amination of cyclic amides and cyclic ureas.
[reaction: see text] An efficient one-step amination of cyclic amides and ureas has been developed. Treatment of cyclic amides and cyclic ureas with BOP in the presence of DBU in various solvents led to the formation of cyclic amidines and cyclic guanidines in good to excellent yields. Concise syntheses of biologically intriguing kinetin and potent kinase inhibitor olomoucin were thus achieved in just one and two steps, respectively.
Wan
Zhao-Kui
ZK
Chemical and Screening Sciences, Wyeth Research, Cambridge, Massachusetts 02140, USA. zwan@wyeth.com
Wacharasindhu
Sumrit
S
Binnun
Eva
E
Mansour
Tarek
T
D000577:Amides / Q000737:chemistry*; D000578:Amidines / Q000138:chemical synthesis*; D000586:Amination; D002384:Catalysis; D006146:Guanidines / Q000138:chemical synthesis*; D007701:Kinetin / Q000138:chemical synthesis*; D015394:Molecular Structure; D014508:Urea / Q000737:chemistry*
D000577:Amides; D000578:Amidines; D006146:Guanidines; C090046:olomoucine; D014508:Urea; D007701:Kinetin