A New Approach to the Synthesis of Biginelli Compounds and Their Analogues

Anatoly Shutalev; Nikolay Kurochkin

doi:10.3390/ecsoc-8-01942

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Synthesis of 5-R-thio, 5-R-sulfinyl, 5-R-sulfonyl and 5-di(R-oxy)phosphoryl Substituted Hydrogenated Pyrimidine-2-thiones/ones

A New Approach to the Synthesis of Biginelli Compounds and Their Analogues

Anatoly D. Shutalev

^*,

Nikolay N. Kurochkin

¹ Department of Organic Chemistry, M.V. Lomonosov State Academy of Fine Chemical Technology, 119571 Moscow, Russian Federation

Published: 01 November 2004 by MDPI in The 8th International Electronic Conference on Synthetic Organic Chemistry session General Organic Synthesis

https://doi.org/10.3390/ecsoc-8-01942

Abstract: A new synthesis of esters of 2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acids and some related compounds has been developed. The synthesis is based on reaction of a-tosyl-substituted phenyl carbamates with enolates of b-oxoesters or 1,3-dicarbonyl compounds followed by treatment of the obtained products with ammonia and dehydration of the resulting 4-hydroxyhexahydropyrimidin-2-ones.

Keywords: a-tosyl-substituted phenyl carbamates; b-oxoesters; 1,3-dicarbonyl compounds; 2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylates; Biginelli compounds; 5-acyl-1,2,3,4-tetrahydropyrimidin-2-ones; 4-hydroxy-2-oxohexahydropyrimidine-5-carboxylates; 5-acyl-4-hydroxyhexahydropyrimidin-2-ones; ureides; 2-oxotetrahydro-1,3-oxazine-2-carboxylates

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Anatoly Shutalev

Nikolay Kurochkin