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

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Roesner, S orcid iconORCID: 0000-0003-2143-4708 (2026) 1,2-Diazetidines − Structure, Synthesis, and Functionalization. European Journal of Organic Chemistry, 29 (19). ISSN 1434-193X

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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.

Item Type: Article
Uncontrolled Keywords: cyclic hydrazines; diazetidines; nitrogen heterocycles; small ring systems; synthetic methods; 3402 Inorganic Chemistry; 3405 Organic Chemistry; 34 Chemical Sciences; Minority Health; Health Disparities; Health Disparities and Racial or Ethnic Minority Health Research; 0304 Medicinal and Biomolecular Chemistry; 0305 Organic Chemistry; Organic Chemistry; 3404 Medicinal and biomolecular chemistry; 3405 Organic chemistry
Subjects: R Medicine > RS Pharmacy and materia medica
Divisions: Pharmacy and Biomolecular Sciences
Publisher: Wiley
Date of acceptance: 12 March 2026
Date of first compliant Open Access: 18 June 2026
Date Deposited: 18 Jun 2026 08:46
Last Modified: 18 Jun 2026 08:46
DOI or ID number: 10.1002/ejoc.70442
URI: https://researchonline.ljmu.ac.uk/id/eprint/28868
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