Polymer-supported stereoselective synthesis of benzimidazolinopiperazinones.
We describe the efficient synthesis of 4,7,8,10-tetrasubstituted-(((4S,10aS)-3-oxo-3,4,10,10a-tetrahydrobenzo[4,5]imidazo[1,2-a]pyrazin-2(1H)-yl)alkyl)amides on solid phase via tandem N-acyliminium ion cyclization-nucleophilic addition reactions. The synthesis proceeded with complete stereocontrol of a newly formed stereogenic center, provided crude material of high purity, and used commercially available building blocks under mild reaction conditions.
Department of Organic Chemistry, Institute of Molecular and Translational Medicine, Faculty of Science, Palacký University, 17. Listopadu 12, 771 46 Olomouc, Czech Republic.
Naděžda
N
Cankařová
Viktor
V
Krchňák
D001562:Benzimidazoles / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D015394:Molecular Structure; D010879:Piperazines / Q000138:chemical synthesis* / Q000737:chemistry; D011108:Polymers / Q000737:chemistry*; D013237:Stereoisomerism
D001562:Benzimidazoles; D010879:Piperazines; D011108:Polymers