1407674-59-2Relevant academic research and scientific papers
Catalytic ugi-type condensation of α-isocyanoacetamide and chiral cyclic imine: Access to asymmetric construction of several heterocycles
Xia, Liang,Li, Sheng,Chen, Ruijiao,Liu, Kai,Chen, Xiaochuan
, p. 3120 - 3131 (2013/06/26)
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.
An ugi-type condensation of α-isocyanoacetamide and chiral cyclic imine under a new catalytic system
Li, Sheng,Chen, Ruijiao,Liu, Xiubing,Pan, Li,Xia, Liang,Chen, Xiaochuan
supporting information; experimental part, p. 1985 - 1989 (2012/09/22)
A new catalytic Ugi-type condensation of α-isocyanoacetamide and chiral cyclic imine is developed, where the combination of phenyl phosphilic acid and trifluoroethanol is exploited to promote the Ugi-type condensation with α-isocyanoacetamide for the first time. Under this new catalytic system, the reaction using the cyclic imines as relatively inertial substrates proceed well, and chiral 3-oxazolyl-morpholin/piperazine-2-one derivatives are synthesized with high yield and stereoselectivity. Furthermore, transformation of the condensation product to a novel fused tricyclic structure is attempted initially by treatment with maleic anhydride. Georg Thieme Verlag Stuttgart · New York.
