Synlett 2024; 35(18): 2107-2112
DOI: 10.1055/a-2283-5749
letter

A Practical Method for the Synthesis of Mesoionic 1,3-Diaryltetrazolium Derivatives Bearing a para-Substituted Phenyl Group at the 1- or 3-Position from Anilines

,
Financial support for this work by the Sasakawa Scientific Research Grant (28-303) is gratefully acknowledged.


Zoom Image

Abstract

A simple, economical, and safe method for the synthesis of mesoionic 1,3-diaryltetrazolium derivatives bearing a para-substituted phenyl group at the 1- or 3-position via thiosemicarbazides was established. Such compounds were directly obtained from the corresponding para-substituted anilines instead of aryl isothiocyanates and arylhydrazines. The newly synthesized mesoionic compounds were successfully converted into the corresponding nitrosotetrazolium salts, which were utilized as catalysts for oxidation of an aliphatic alcohol and analyzed by cyclic voltammetry to determine the correlation between the catalytic efficiencies and redox potentials. The proposed method can be widely applied and is valuable for investigating the substituent effects in mesoionic and related compounds.

Supporting Information



Publication History

Received: 27 August 2023

Accepted after revision: 07 March 2024

Accepted Manuscript online:
07 March 2024

Article published online:
26 March 2024

© 2024. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany