Efficient one-pot synthesis of 2,3-dihydropyrimidinthiones via multicomponent coupling of terminal alkynes, elemental sulfur, and carbodiimides

Zitao Wang; Yang Wang; Wen-Xiong Zhang; Zhaomin Hou; Zhenfeng Xi

doi:10.1021/ja9069419

Efficient one-pot synthesis of 2,3-dihydropyrimidinthiones via multicomponent coupling of terminal alkynes, elemental sulfur, and carbodiimides

J Am Chem Soc. 2009 Oct 28;131(42):15108-9. doi: 10.1021/ja9069419.

Authors

Zitao Wang¹, Yang Wang, Wen-Xiong Zhang, Zhaomin Hou, Zhenfeng Xi

Affiliation

¹ Beijing National Laboratory for Molecular Sciences and Key Laboratory of Bioorganic Chemistry and Molecular Engineering of the Ministry of Education, College of Chemistry, Peking University, Beijing 100871, China.

PMID: 19919156
DOI: 10.1021/ja9069419

Abstract

An organolithium-promoted multicomponent reaction (MCR) involving readily available terminal alkynes, elemental sulfur, and carbodiimides has been achieved for the first time. This MCR offers an atom-economic route to 2,3-dihydropyrimidinthiones which are difficult to access by other means via an interesting and useful C=N double bond cleavage and an sp(3) C-H bond functionalization of carbodiimides.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkynes / chemistry*
Carbodiimides / chemistry*
Models, Molecular
Molecular Structure
Pyrimidines / chemical synthesis*
Sulfur / chemistry*
Thiones / chemical synthesis*

Substances

Alkynes
Carbodiimides
Pyrimidines
Thiones
Sulfur