Work

1,2‐Diazetidines − Structure, Synthesis, and Functionalization

Year: 2026

Type: article

Abstract: 1,2‐Diazetidines are saturated four‐membered heterocycles featuring two adjacent nitrogen atoms. Despite their promising potential as rigid molecular scaffolds for drug discovery, their synthesis and reactivity remain largely unexplored. This review summarizes their three‐dimensional structural features, which have been characterized using various spectroscopic and crystallographic methods. Current synthetic approaches of 1,2‐diazetidines fall into three main categories: (i) [2 + 2] cycloadditions between azo compounds and electron‐rich olefins, (ii) photochemical ring contraction of dihydropyridazines, and (iii) intramolecular ring closure of hydrazine derivatives, the latter enabling stereocontrol at the four‐membered ring. Finally, the reactivity and functionalization of these cyclic hydrazines are discussed, including derivatization at both nitrogen atoms.

Source: European Journal of Organic Chemistry

DOI: 10.1002/ejoc.70442

Author: Stefan Roesner

Institution: Liverpool John Moores University

Language: English

Topic: Structural and Chemical Analysis of Organic and Inorganic Compounds

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,330

Funders: University of Warwick, Liverpool John Moores University, Engineering and Physical Sciences Research Council