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Updated: May 2, 2026

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
Published on: July 28, 2022
A concomitant allylic azide rearrangement/intramolecular azide-alkyne cycloaddition sequence
Rakesh H Vekariya1, Ruzhang Liu, Jeffrey Aubé
1Department of Medicinal Chemistry, University of Kansas , Lawrence, Kansas 66045, United States.
This study demonstrates controlling triazole formation using intramolecular Huisgen cycloadditions. Reaction conditions, whether thermal or copper-catalyzed, dictate whether substituted triazoles or macrocyclic products are formed.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
Background:
- The Huisgen cycloaddition is a key reaction in organic synthesis.
- Controlling the stereochemistry and product outcome of cycloaddition reactions is crucial for developing new synthetic methodologies.
Purpose of the Study:
- To investigate the intramolecular Huisgen cycloaddition of allylic azides with alkynes.
- To explore the influence of reaction conditions on the product distribution and stereochemistry.
Main Methods:
- Utilizing an intramolecular Huisgen cycloaddition reaction.
- Comparing thermal versus copper(I)-catalyzed reaction conditions.
- Analyzing the stereoisomeric products formed.
Main Results:
- High yields of substituted triazoles were achieved.
- Thermal conditions led to stereoisomeric vinyl-substituted triazoloxazines, dependent on azide precursor cycloaddition rates.
- Copper(I)-catalyzed conditions resulted in dimerized macrocyclic products.
Conclusions:
- The reaction pathway and product outcome can be effectively controlled by altering reaction conditions.
- This work provides a method for selectively synthesizing different triazole-based structures.
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