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Synthesis 2010(23): 3943-3953  
DOI: 10.1055/s-0030-1258290
REVIEW
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Dihydropyrimidinones and Thiones by Multicomponent Reactions: Strategies Beyond the Classical Biginelli Reaction

Jie-Ping Wan*, Yunyun Liu
College of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang, Jiangxi 330022, P. R. of China
Fax: +86(791)8120380; e-Mail: wanjieping@gmail.com;
Further Information

Publication History

Received 19 July 2010
Publication Date:
07 October 2010 (online)

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Abstract

The three-component Biginelli reaction for the synthesis of dihydropyrimidinone and corresponding dihydropyrimidine­thiones (DHPMs) has been known for more than a century. Consistent attention has been paid to the study of Biginelli reaction owing to the significant biological and pharmaceutical merits of DHPMs. In the view of molecular diversity, the development of new multicomponent reactions that provide DHPMs bearing novel functional structures has emerged as a central issue in recent years. This account systematically summarizes the multicomponent reaction syntheses of novel DHPMs that are not accessible through the classical Biginelli reaction.

1 Introduction

2 Synthesis of DHPMs via Modification of Classical Biginelli Substrates

2.1 Using β-Keto Ester Alternatives

2.2 Using Urea/Thiourea Alternatives

2.3 Using Aldehyde Alternatives

3 Synthesis of DHPMs via Other Multicomponent Reactions

4 Conclusions

Key words

dihydropyrimidinone - dihydropyrimidinethione - multicomponent reactions