title: Catalytic Ugi-type condensation of α-isocyanoacetamide and chiral cyclic imine: access to asymmetric construction of several heterocycles.
abstract: Several novel heterocycles have been constructed asymmetrically on the basis of a catalytic Ugi-type condensation of α-isocyanoacetamide and chiral cyclic imine. The combination of phenylphosphilic acid and trifluoroethanol is exploited to promote an Ugi-type reaction with α-isocyanoacetamide for the first time. By means of this reaction, chiral 3-oxazolyl morpholin-2-one/piperazin-2-one derivatives are synthesized with high yields and excellent stereoselectivities. As electron-rich azadienes, these condensation products are further transformed to fused tricyclic frameworks by treatment with appropriate dienophiles such as maleic anhydride and unsaturated acyl chlorides via domino processes. Moreover, a one-pot, three-component synthesis of the chiral tricyclic frameworks from isocyanoacetamide, imine, and maleic anhydride is also feasible.
authors: Key Laboratory of Green Chemistry & Technology of the Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, People's Republic of China.
authors: Liang
authors: L
authors: Xia
authors: Sheng
authors: S
authors: Li
authors: Ruijiao
authors: R
authors: Chen
authors: Kai
authors: K
authors: Liu
authors: Xiaochuan
authors: X
authors: Chen
mesh_terms: D002384:Catalysis; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D007097:Imines / Q000737:chemistry*; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*
chemical_list: D006571:Heterocyclic Compounds; D007097:Imines; D009570:Nitriles; C031594:2-cyanoacetamide