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Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
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A new approach to the 8b-azaacenaphthylene ring system
Anushree Kamath1, Charles-Henry Fabritius, Christian Philouze
1SERCO, Département de Chimie Moléculaire, Univ. Grenoble Alpes, ICMG FR-2607, CNRS, UMR-5616, F-38041 Grenoble, France. Philippe.Delair@ujf-grenoble.fr.
Organic & Biomolecular Chemistry
|August 18, 2015
Summary
This study introduces a novel stereoselective synthesis for the 8b-azaacenaphthylene core. Key steps include a dichloroketene cycloaddition and aza-Prins cyclization for efficient construction.
Area of Science:
- Organic Chemistry
- Synthetic Methodology
Background:
- The 8b-azaacenaphthylene scaffold is a relevant heterocyclic motif.
- Developing stereoselective routes to complex ring systems is crucial in organic synthesis.
Purpose of the Study:
- To establish a novel and stereoselective synthetic pathway to the 8b-azaacenaphthylene ring system.
- To showcase the utility of key stereoselective transformations in constructing this scaffold.
Main Methods:
- Utilized a dichloroketene-enol ether [2 + 2] cycloaddition reaction.
- Incorporated a vinylogous Mannich reaction as a key step.
- Employed an aza-Prins cyclization for stereochemical control.
Main Results:
- Successfully developed a stereoselective approach to the 8b-azaacenaphthylene core.
- Demonstrated the effectiveness of the combined cycloaddition, Mannich, and aza-Prins reactions.
- Achieved controlled stereochemistry in the synthesis.
Conclusions:
- The described synthetic route provides an efficient method for accessing the 8b-azaacenaphthylene ring system.
- The key transformations offer a powerful strategy for stereoselective synthesis of related heterocycles.
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