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Synthesis 2019; 51(09): 2014-2022
DOI: 10.1055/s-0037-1611712
DOI: 10.1055/s-0037-1611712
paper
Heterogeneous Copper(I)-Catalyzed Cascade Addition–Oxidative Cyclization of Nitriles with 2-Aminopyridines or Amidines: Efficient and Practical Synthesis of 1,2,4-Triazoles
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 (online)
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.
Key words
copper - 1,2,4-triazole - oxidative cyclization - heterogeneous catalysis - cascade reactionSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1611712.
- Supporting Information
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