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Vinylation of α-Aminoazoles with Triethylamine: A General Strategy to Construct Azolo[1,5-a]pyrimidines with a Nonsubstituted Ethylidene Fragment

Qinghe Gao, Zhenhua Sun, Qinfei Xia, Ruonan Li, Wenlong Wang, Siwei Ma, Yixin Chai, Manman Wu, Wei Hu, Péter Ábrányi-Balogh, György M. Keserű and Xinya Han*

*School of Chemistry and Chemical Engineering, Anhui University of Technology, Maanshan, Anhui 243002, P. R. China, Email: xinyahanahut.edu.cn

Q. Gao, Z. Sun, Q. Xia, R. Li, W. Wang, S. Ma, Y. Chai, M. Wu, W. Hu, P. Ábrányi-Baloghm G. M. Keserű, X. Han, Org. Lett., 2021, 23, 2621-2625.

DOI: 10.1021/acs.orglett.1c00571 (free Supporting Information)


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Abstract

Pharmaceutically important azolo[1,5-a]pyrimidines can be synthesized from widely available 3- or 5-aminoazoles, aldehydes, and triethylamine. The key is the in situ generation of an acyclic enamine followed by an annulation reaction. This strategy is capable of constructing a range of 5,6-unsubstituted pyrazolo[1,5-a]pyrimidines and [1,2,4]triazolo[1,5-a]pyrimidines.


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proposed mechanism



Key Words

fused N-heterocycles, multicomponent reactions, DTBP


ID: J54-Y2021