A Convenient Synthesis of 1,5-Fused 1,2,4-Triazoles from N-Arylamidines via Chloramine-T Mediated Intramolecular Oxidative N–N Bond Formation

Ashish Bhatt; Rajesh K. Singh; Ravi Kant; Bhupendra K. Sarma

doi:10.1055/s-0037-1611906

Synthesis, Table of Contents

Synthesis 2019; 51(20): 3883-3890
DOI: 10.1055/s-0037-1611906

paper

A Convenient Synthesis of 1,5-Fused 1,2,4-Triazoles from N-Arylamidines via Chloramine-T Mediated Intramolecular Oxidative N–N Bond Formation

Ashish Bhatt ∗

^aDepartment of Chemistry, Mewar University, Chittorgarh, Rajasthan-312901, India Email: Itsbhatt2007@yahoo.co.in

,

Rajesh K. Singh

^bDepartment of Pharmacy, Mewar University, Chittorgarh, Rajasthan-312901, India

,

Ravi Kant

^aDepartment of Chemistry, Mewar University, Chittorgarh, Rajasthan-312901, India Email: Itsbhatt2007@yahoo.co.in

,

Bhupendra K. Sarma

^aDepartment of Chemistry, Mewar University, Chittorgarh, Rajasthan-312901, India Email: Itsbhatt2007@yahoo.co.in

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Abstract

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Abstract

A convenient synthesis of 1,5-fused 1,2,4-triazoles from readily available N-arylamidines is reported. The reaction is efficiently promoted by chloramine-T to afford the desired products mostly in high yields and in relatively short time, through direct metal-free oxidative N−N bond formation. The mild nature of the synthesis and short reaction time are notable advantages of the developed protocol. This protocol is effective toward various substrates having different functionalities.

Key words

N-arylamidine - [1,2,4]triazolo[1,5-a]pyridine - [1,2,4]triazolo[1,5-a]pyrazine - [1,2,4]triazolo[1,5-a]pyrimidine - chloramine-T - ethanol

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