An Electrochemical Way to Generate Amphiphiles from Hydrazones for the Synthesis of 1,2,4-Triazole Scaffold Cyclic Compounds

Abstract

An electro-oxidative cyclization pathway in which hydrazones are selected as starting materials to generate amphiphiles by reacting with benzylamines and benzamides was reported. This strategy successfully prepared a series of 1,2,4-triazoles in satisfactory yields. Moreover, the use of cheap stainless steel as the anode, the feasibility to conduct the transformation as a one-pot reaction and the proof that scaling-up these reactions is possible make this transformation attractive for potential application in industry.

Keywords: 1,2,4-trizaole; amphiphiles; cyclization; electrooxidation; one-pot reaction.

Scheme 1

Different methods for the synthesis of 1,2,4‐triazoles.

Scheme 2

Our strategies for the construction of ring compounds.

Scheme 3

One‐pot reaction and scale‐up experiments (SSC=stainless steel cathode).

Scheme 4

Control experiments (SSC=stainless steel cathode, BHT=3,5‐di‐tert‐butyl‐4‐hydroxytoluol).

Scheme 5

Proposed mechanism for the transformation (DDQ=2,3‐Dichloro‐5,6‐dicyano‐1,4‐benzoquinone).

Scheme 6

Further confirmatory experiment of our proposed strategy (SSC=stainless steel cathode).