Oxidative Dehydrosulfurative Cross-Coupling of 3,4-Dihydropyrimidine-2-thiones with Alkynes for Access to 2-Alkynylpyrimidines

Authors

Ngoc Son Le Pham, Chungnam National University
Hyunik Shin, Yonsung Fine Chemicals R and D Center
Jun Yong Kang, University of Nevada, Las VegasFollow
Jeong-Hun Sohn, Chungnam National UniversityFollow

Document Type

Article

Publication Date

3-11-2020

Publication Title

Journal of Organic Chemistry

Volume

85

First page number:

5087

Last page number:

5096

Abstract

A reaction method is described for the one-step synthesis of 2-alkynylpyrimidines from 3,4-dihydropyrimidin-1H-2-thiones (DHPMs) via dehydrosulfurative Sonogashira cross-coupling with concomitant oxidative dehydrogenation using a Pd/Cu catalytic system. Together with the ready availability of DHPMs possessing various substituents at the C4–C6 positions, this transformation offers rapid and general access to diverse 2-alkynylpyrimidine derivatives.

Disciplines

Chemistry | Organic Chemistry | Physical Sciences and Mathematics

Language

English

Repository Citation

Pham, N. S., Shin, H., Kang, J. Y., Sohn, J. (2020). Oxidative Dehydrosulfurative Cross-Coupling of 3,4-Dihydropyrimidine-2-thiones with Alkynes for Access to 2-Alkynylpyrimidines. Journal of Organic Chemistry, 85 5087-5096.
http://dx.doi.org/10.1021/acs.joc.0c00091