Work

Blue Light-Induced N–H Functionalization of Tetrazoles with Aryldiazoacetates: Access to 1,5-Disubstituted Regioisomers

Year: 2026

Type: article

Abstract: A novel method for synthesizing 1,5-disubstituted tetrazole derivatives via blue light-promoted N–H insertion of aryldiazoacetates into NH-tetrazoles is presented. The reaction affords mixtures of regioisomeric products, with a predominance of 1,5-disubstituted derivatives. A comprehensive investigation of reaction conditions and substrate effects influencing regioselectivity has been performed. These findings provide new insights into the regioselectivity of NH-tetrazole alkylation and reveal potential applications of this approach in the assembly of tetrazole-containing scaffolds.

Source: Synthesis

DOI: 10.1055/a-2837-6310

Authors: Valentin Radiupov, Grigory Kantin, Stepan Meshalkin, Elena Tupikina, Dmitry Dar'in

Institutions: St Petersburg University, Saint-Petersburg Research Institute of Phthisiopulmonology

Language: English

Topic: Synthesis of Tetrazole Derivatives

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: gold

Funders: Saint Petersburg State University, Russian Science Foundation, Division of Materials Research

Awards: G3513192780, G474167555