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Synthesis 2019; 51(16): 3091-3100
DOI: 10.1055/s-0037-1610710
DOI: 10.1055/s-0037-1610710
paper
A Highly Efficient Heterogeneous Copper-Catalyzed Oxidative Cyclization of Benzylamines and 1,3-Dicarbonyl Compounds To Give Trisubstituted Oxazoles
We thank the National Natural Science Foundation of China (No. 21462021), the Natural Science Foundation of Jiangxi Province (No. 20161BAB203086), and the Ministry of Education (Key Laboratory of Functional Small Organic Molecules, No. KLFS-KF-201704) for financial support.Further Information
Publication History
Received: 24 February 2019
Accepted after revision: 02 April 2019
Publication Date:
02 May 2019 (online)
Abstract
The heterogeneous copper-catalyzed cascade oxidative cyclization between benzylamines and 1,3-dicarbonyl compounds was achieved by using the 3-(2-aminoethylamino)propyl-functionalized MCM-41-immobilized copper(II) complex [MCM-41-2N-Cu(OAc)2] as catalyst and t-BuOOH (TBHP) as oxidant, with iodine as additive, under mild conditions, yielding a wide variety of 2,4,5-trisubstituted oxazoles in mostly good to excellent yields. This heterogeneous copper catalyst can be facilely prepared via a simple two-step procedure from readily available and inexpensive reagents and exhibits a slightly higher activity than Cu(OAc)2. MCM-41-2N-Cu(OAc)2 is also easy to recover and can be recycled up to eight times with almost consistent activity. The reaction is the first example of heterogeneous copper-catalyzed intermolecular cyclization for the construction of polysubstituted oxazoles.
Key words
copper - 2,4,5-trisubstituted oxazole - oxidative cyclization - heterogeneous catalysis - cascade reactionSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610710.
- Supporting Information
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For selected examples, see:
For selected examples, see: