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Synthesis 2017; 49(17): 3985-3997
DOI: 10.1055/s-0036-1589045
DOI: 10.1055/s-0036-1589045
paper
Base-Mediated Ring Opening of meso-Epoxides with 4-Aryl-NH-1,2,3-triazoles: Synthesis of trans-2-(Aryltriazolyl)cycloalkanols
Further Information
Publication History
Received: 30 April 2017
Accepted after revision: 03 May 2017
Publication Date:
19 July 2017 (online)
Abstract
A novel method of nucleophilic ring-opening of meso-epoxides with 4-aryl-NH-1,2,3-triazoles has been developed under metal-free conditions. The epoxide-ring opening process were carried out in the presence of organic bases (DABCO/Et3N) in acetonitrile at 85 °C to afford a regioisomeric mixture of trans-2-(4-aryl-2H-1,2,3-triazol-2-yl)cycloalkanols (2,4-disubstituted triazoles) as major adducts and trans-2-(4-aryl-1H-1,2,3-triazol-1-yl)cycloalkanols (1,4-disubstituted triazoles) as minor adducts in excellent combined chemical yields (isolated yield up to 99%).
Supporting Information
- Supporting information for this article is available online at https://doi.org /10.1055/s-0036-1589045.
- Supporting Information
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For reviews on the CuAAC and its applications, see:
For seminal papers and representative examples of copper(I)-catalyzed azide-alkyne cycloaddition, see: