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Updated: May 22, 2025

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Ruthenium-Catalyzed Enyne Metathesis: An Entry to Functionalized Azaborine Heterocycles
Keyu Mao1, Fabien Fontaine-Vive1, Romain Melot1
1Université Côte d'Azur, Institut de Chimie de Nice, Valrose Park, 06108, Nice Cedex 2, France.
Abstract:
An unprecedented and green synthetic route for the preparation of functionalized polycyclic azaborine skeletons via a ruthenium-mediated ring-closing enyne metathesis transformation of alkynyl B-anthranilamide (aam) is reported. A variety of B(aam)-bridge enyne derivatives were engaged with the Grubbs-II catalyst, affording the corresponding exo-cyclic compounds (28 novel derivatives). The methodology was efficiently optimized in dimethyl carbonate as green solvent and provided a direct access to functionalized boronated scaffolds displaying dienes which can be further functionalized. In addition, computational analysis of several of the cores synthesized in this study revealed an isoelectronic and isostructural relationship with potential isosteres.
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