Base-Mediated Ring Opening of meso-Epoxides with 4-Aryl-NH-1,2,3-triazoles: Synthesis of trans-2-(Aryltriazolyl)cycloalkanols

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%).

Key words

epoxides - heterocycles - organic bases - ring opening - triazoles

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