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Convergent and Rapid Assembly of Substituted 2-Pyridones through Formation of N-Alkenyl Alkynylamides Followed by Gold-Catalyzed Cycloisomerization

Hidetomo Imase, Keiichi Noguchi, Masao Hirano and Ken Tanaka*

*Department of Applied Chemistry, Graduate School of Engineering, and Instrumentation Analysis Center, Tokyo University of Agriculture and Technology, Koganei, Tokyo 184-8588, Japan, Email: tanaka-kcc.tuat.ac.jp

H. Imase, K. Noguchi, M. Hirano, K. Tanaka, Org. Lett., 2008, 10, 3563-3566.

DOI: 10.1021/ol801466f (free Supporting Information)


Abstract

Formation of N-alkenyl alkynylamides by N-acylation of imines with alkynoyl chlorides and the subsequent cationic Au(I)/PPh3-catalyzed cycloisomerization allows a convergent and rapid assembly of substituted 2-pyridones.

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Key Words

2-pyridones, amides, Ghosez's reagent


ID: J54-Y2008-2300