Stereoselective pyrroline-ring formation through the cyclization of conjugated azomethine ylides at the periphery of pyrido[1,2-a]pyrimidine system |
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| Authors: | Michihiko Noguchi Masashi ShiraiKuniko Nakashima Ichiro AraiAkiko Nishida Hidetoshi YamamotoAkikazu Kakehi |
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| Affiliation: | a Department of Applied Chemistry, Faculty of Engineering, Yamaguchi University, Tokiwadai, Ube 755-8611, Japan
b Department of Chemistry and Material Engineering, Faculty of Engineering, Shinshu University, Wakasato, Nagano 380-8553, Japan |
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| Abstract: | The thermal reaction of N-benzyl-N-[3-(N-substituted imino)methyl-4-oxo-4H-pyrido[1,2-a]pyrimidin-2-yl]amino acid esters, generated from aldehyde esters and primary amines, provides 2,3-dihydropyrido[1,2-a]pyrrolo[2,3-d]pyrimidin-4(1H)-one derivatives effectively and stereoselectively. Therein, the stereoselective generation of conjugated azomethine ylides from the imine esters and their cyclization is essential for the pyrroline-ring formation. |
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| Keywords: | pyrroline-ring formation conjugated azomethine ylide cyclization chirality transfer |
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