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Generation of functionalized azomethine ylides and their application to stereoselective heterocycle synthesis: An equivalent process of C-unsubstituted nitrile ylide …

K Kawashima, A Kakehi, M Noguchi

Index: Kawashima, Keisuke; Kakehi, Akikazu; Noguchi, Michihiko Tetrahedron, 2007 , vol. 63, # 7 p. 1630 - 1643

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Citation Number: 25

Abstract

The synthetic process equivalent to C-unsubstituted (CH) nitrile ylides cycloaddition reaction is achieved via cycloaddition of NH-azomethine ylide and the following fission reaction of the cycloadducts under acidic conditions. Cycloaddition of NH-azomethine ylide generated by a thermal 1, 2-prototropy in 4-oxo-4H-pyrido [1, 2-a] pyrimidine-3-carbaldehyde system with maleimides provides proline derivatives under extremely mild conditions. Heating ...