Related Experiment Video
Updated: Jan 12, 2026

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Diazacyclobutene Ring Cleavage Provides 1,2-Diazetidin-3-ones via Intramolecular Nucleophilic Cyclization
Monireh Noori1, Samuel Kwain1, Brock A Miller2
1Department of Chemistry, Clemson University, Clemson, South Carolina 29634, United States.
Abstract:
We report an efficient two-step strategy for the synthesis of 1,2-diazetidin-3-ones (or aza-β-lactams) from thiolated diazacyclobutene intermediates. The transformation involves acid-promoted ring scission, followed by base-induced intramolecular nucleophilic cyclization, affording the desired diazetidinones in good yields. This method offers straightforward access to a structurally unique and underexplored four-membered heterocycle, expanding the synthetic toolbox for strained nitrogen-containing ring systems.
More Related Videos
Related Concept Videos
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Cycloaddition Reactions: Overview
Intramolecular Claisen Condensation of Dicarboxylic Esters: Dieckmann Cyclization
Mass Spectrometry: Cycloalkene Fragmentation

