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DOI: 10.1055/s-0042-1751554
Exploring the Reactivity of Substituted [(Allyloxy)methyl]phosphonates in Cycloaddition and Coupling Reactions
The authors are deeply indebted to the Tunisian Ministry of Higher Education and Scientific Research, the Université de Tunis El Manar (Tunisia), the Centre National de la Recherche Scientifique (CNRS, France), and the Université de Nantes (France) for their support.
Abstract
This paper describes the versatility of substituted [(allyloxy)methyl]phosphonates to open the way to the synthesis of original phosphonated molecules with heterocyclic architectures. In 1,3-dipolar cycloaddition reactions with nitrile oxides, nitrile imines, and nitrones, these [(allyloxy)methyl]phosphonates react as dipolarophiles to give, regioselectively, the corresponding isoxazolines, pyrazolines, and isoxazolidines. Transition-metal-catalyzed reactions, including inter- or intramolecular Heck coupling, provided access to cinnamyl- and indenyl-linked moieties and phosphonated benzo-fused oxacycles, respectively. Additionally, ring-closing metathesis reactions enabled the synthesis of 2,5-dihydrofurans with the phosphonate group at the anomeric position. In this work, 51 novel phosphorylated heterocyclic compounds, which may find significance in the pharmaceutical and agrochemical fields, were prepared.
Key words
organophosphorus compounds - 1,3-dipolar cycloaddition - Heck coupling reaction - radical cyclization - metathesisSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0042-1751554.
- Supporting Information
Publication History
Received: 21 November 2023
Accepted after revision: 05 January 2024
Article published online:
15 February 2024
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