Synlett 2018; 29(10): 1395-1399
DOI: 10.1055/s-0036-1591565
letter
© Georg Thieme Verlag Stuttgart · New York

Copper-Catalyzed Cascade Synthesis of [1,2,4]-Triazoloquinazolinones

Zhenbang Lou
a   School of Chemistry and Chemical Engineering, Beijing Institute of Technology, Beijing 100081, P. R. of China   Email: fuhua@mail.tsinghua.edu.cn
b   Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing 100084, P. R. of China
,
Ningning Man
b   Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing 100084, P. R. of China
,
Haijun Yang
b   Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing 100084, P. R. of China
,
Changjin Zhu
a   School of Chemistry and Chemical Engineering, Beijing Institute of Technology, Beijing 100081, P. R. of China   Email: fuhua@mail.tsinghua.edu.cn
,
Hua Fu  *
a   School of Chemistry and Chemical Engineering, Beijing Institute of Technology, Beijing 100081, P. R. of China   Email: fuhua@mail.tsinghua.edu.cn
b   Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing 100084, P. R. of China
› Author Affiliations
Financial support from the National Natural Science Foundation of China (Grant No. 21772108) is gratefully acknowledged.
Further Information

Publication History

Received: 04 February 2018

Accepted after revision: 12 March 2018

Publication Date:
20 April 2018 (online)


Abstract

An efficient and practical method for the synthesis of 1,2,4-triazolo[5,1-b]quinazolin-9(3H)-ones has been developed via the copper-catalyzed domino reactions of readily available substituted N′-acetyl-2-bromobenzohydrazides with cyanamide. The protocol uses inexpensive CuI as the catalyst, and no other ligand or additive was required. The target products were prepared in good to excellent yields with tolerance of various functional groups.

Supporting Information