Related Experiment Video
Updated: Nov 11, 2025

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Effective microwave-assisted approach to 1,2,3-triazolobenzodiazepinones via tandem Ugi reaction/catalyst-free
Maryna O Mazur1,2, Oleksii S Zhelavskyi1,3, Eugene M Zviagin1,4
1Division of Chemistry of Functional Materials, State Scientific Institution "Institute for Single Crystals" of National Academy of Sciences of Ukraine, 60 Nauky Ave, Kharkiv, 61072, Ukraine.
Abstract:
A novel catalyst-free synthetic approach to 1,2,3-triazolobenzodiazepinones has been developed and optimized. The Ugi reaction of 2-azidobenzaldehyde, various amines, isocyanides, and acids followed by microwave-assisted intramolecular azide-alkyne cycloaddition (IAAC) gave a series of target heterocyclic compounds in moderate to excellent yields. Surprisingly, the normally required ruthenium-based catalysts were found to not affect the IAAC, only making isolation of the target compounds harder while the microwave-assisted catalyst-free conditions were effective for both terminal and non-terminal alkynes.
Related Concept Videos
Preparation of 1° Amines: Azide Synthesis
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
Cycloaddition Reactions: Overview
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
Cycloaddition Reactions: MO Requirements for Thermal Activation
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

