Synthesis 2019; 51(09): 2014-2022
DOI: 10.1055/s-0037-1611712
paper
© Georg Thieme Verlag Stuttgart · New York

Heterogeneous Copper(I)-Catalyzed Cascade Addition–Oxidative Cyclization of Nitriles with 2-Aminopyridines or Amidines: Efficient and Practical Synthesis of 1,2,4-Triazoles

Jianhui Xia
,
Xue Huang
,
Key Laboratory of Functional Small Organic Molecule, Ministry of Education and College of Chemistry & Chemical Engineering, Jiangxi Normal University, Nanchang 330022, P. R. of China   Email: mzcai@jxnu.edu.cn
› Author Affiliations
We thank the National Natural Science Foundation of China (No. 21462021), the Natural Science Foundation of Jiangxi Province of China (No. 20161BAB203086) and Key Laboratory of Functional Small Organic Molecule, Ministry of Education (No. KLFS-KF-201704) for financial support.
Further Information

Publication History

Received: 23 October 2018

Accepted after revision: 05 December 2018

Publication Date:
18 February 2019 (eFirst)

Abstract

The heterogeneous cascade addition-oxidative cyclization of nitriles with 2-aminopyridines or amidines was achieved in 1,2-dichlorobenzene or DMSO at 120–130 °C by using a 1,10-phenanthroline-functionalized MCM-41-supported copper(I) complex [Phen-MCM-41-CuBr] as the catalyst and air as the oxidant. The approach was used to generate a wide variety of 1,2,4-triazole derivatives in mostly high yields. This heterogeneous copper(I) catalyst could be easily prepared in a two-step procedure from commercially or readily available and inexpensive reagents and it exhibited higher catalytic activity than the CuBr/1,10-Phen system. Phen-MCM-41-CuBr was also easy to recover and was recyclable up to eight times with almost consistent activity.

Supporting Information

 
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