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1. Highly diastereoselective domino synthesis of 6-spirosubstituted pyrido[2,3-d]pyrimidine derivatives in water.

Author

Jiang B, Cao LJ, Tu SJ, Zheng WR, and Yu HZ

Subjects
Aldehydes chemistry, Barbiturates chemistry, Microwaves, Models, Molecular, Pyrimidines chemistry, Spiro Compounds chemistry, Stereoisomerism, Combinatorial Chemistry Techniques methods, Pyrimidines chemical synthesis, Spiro Compounds chemical synthesis, Water chemistry
Abstract

A highly diastereoselective domino reaction of 2,6-diaminopyrimidine-4-one with structurally diverse aryl aldehydes and various barbituric acids in water under microwave irradiation is described. The products are 6-spiro-substituted pyrido[2,3-d]pyrimidines with high diastereoselectivities (up to 99: 1) in which the major diastereomer bears a cis relationship between substituents at the 5- and 7-positions. Furthermore, the mechanism for diastereoselectivity was confirmed by DFT (B3LYP) calculations.

Published
2009
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