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

Ujjawal Kumar Bhagat; Rama Krishna Peddinti; Kamaluddin

doi:10.1055/s-0036-1589045

Synthesis, Inhaltsverzeichnis

Synthesis 2017; 49(17): 3985-3997
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

Ujjawal Kumar Bhagat

Department of Chemistry, Indian Institute of Technology Roorkee, Roorkee-247667, Uttarakhand, India eMail: rkpedfcy@iitr.ac.in eMail: ramakpeddinti@gmail.com

,

Kamaluddin,

Rama Krishna Peddinti*

Department of Chemistry, Indian Institute of Technology Roorkee, Roorkee-247667, Uttarakhand, India eMail: rkpedfcy@iitr.ac.in eMail: ramakpeddinti@gmail.com

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Abstract

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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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Referenzen

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