# Synthesis of Functionalized 1H-Imidazoles via Denitrogenative Transformation of 5-Amino-1,2,3-Triazoles

**Authors:** Pavel S. Gribanov, Anna N. Philippova, Alexander F. Smol’yakov, Diana N. Tukhvatullina, Viktoria A. Vlasova, Maxim A. Topchiy, Andrey F. Asachenko, Sergey N. Osipov

PMC · DOI: 10.3390/molecules30071401 · Molecules · 2025-03-21

## TL;DR

A new method for making 1H-imidazole compounds is developed using a denitrogenative transformation of triazoles.

## Contribution

A novel acid-mediated denitrogenative transformation of 5-amino-1,2,3-triazoles to synthesize 2-substituted 1H-imidazoles is introduced.

## Key findings

- The method involves intramolecular cyclization followed by ring opening and carbene insertion into alcohols.
- The transformation is efficient and occurs under acidic conditions.
- The approach utilizes triazoles generated via dipolar azide−nitrile cycloaddition.

## Abstract

An efficient access to novel 2-substituted 1H-imidazole derivatives was developed based on acid-mediated denitrogenative transformation of 5-amino-1,2,3-triazole derivatives available through dipolar azide−nitrile cycloaddition (DCR). The proposed approach includes intramolecular cyclization of 5-amino-4-aryl-1-(2,2-diethoxyethyl) 1,2,3-triazoles followed by triazole ring opening and insertion of in situ formed carbene intermediate into the O-H bond of different alcohols under acidic conditions.

## Linked entities

- **Chemicals:** 5-amino-1,2,3-triazole (PubChem CID 12295187), 1H-imidazole (PubChem CID 795)

## Full text

_Full body text omitted from this summary view._ Fetch the complete paper as Markdown: https://tomesphere.com/paper/PMC11990592/full.md

## Figures

6 figures with captions in the complete paper: https://tomesphere.com/paper/PMC11990592/full.md

## References

60 references — full list in the complete paper: https://tomesphere.com/paper/PMC11990592/full.md

---
Source: https://tomesphere.com/paper/PMC11990592