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A New Substrate for the Biginelli Cyclocondensation:  Direct Preparation of 5-Unsubstituted 3,4-Dihydropyrimidin-2(1H)-ones from a β-Keto Carboxylic Acid

Jacqueline C. Bussolari and Patricia A. McDonnell

*The R.W. Johnson Pharmaceutical Research Institute, 1000 Route 202, Raritan, New Jersey 08869

J. C. Bussolari, P. A. McDonell, J. Org. Chem., 2000, 65, 6777-6779.

DOI: 10.1021/jo005512a (free Supporting Information)


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Abstract

Oxalacetic acid is an excellent substrate for Biginelli reactions with electron-rich as well as electron-poor aldehydes using TFA in refluxing dichloroethane. The carboxylic acid appendage on C(6) offers functionality capable of a wide range of transformations.

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proposed mechanism



Key Words

Biginelli Cyclocondensation


ID: J42-Y2000