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Stereoselective pyrroline-ring formation through the cyclization of conjugated azomethine ylides at the periphery of pyrido[1,2-a]pyrimidine system

✍ Scribed by Michihiko Noguchi; Masashi Shirai; Kuniko Nakashima; Ichiro Arai; Akiko Nishida; Hidetoshi Yamamoto; Akikazu Kakehi

Publisher: Elsevier Science
Year: 2003
Tongue: French
Weight: 270 KB
Volume: 59
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(03)00657-4

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✦ Synopsis

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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