Synthesis, Inhaltsverzeichnis

Synthesis 2024; 56(10): 1619-1647
DOI: 10.1055/s-0042-1751554

paper

Exploring the Reactivity of Substituted [(Allyloxy)methyl]phosphonates in Cycloaddition and Coupling Reactions

Momtez Jmai

^aLaboratory of Selective Organic & Heterocyclic Synthesis and Biological Activity Evaluation (LR17ES01), Department of Chemistry, Faculty of Sciences of Tunis, University of Tunis El Manar, Tunis 2092, Tunisia

^bUniversité de Nantes, CNRS, CEISAM, UMR 6230, 44000 Nantes, France

,

Virginie Blot ∗

^bUniversité de Nantes, CNRS, CEISAM, UMR 6230, 44000 Nantes, France

,

Monique Mathé-Allainmat

^bUniversité de Nantes, CNRS, CEISAM, UMR 6230, 44000 Nantes, France

,

Mohamed Lotfi Efrit

^aLaboratory of Selective Organic & Heterocyclic Synthesis and Biological Activity Evaluation (LR17ES01), Department of Chemistry, Faculty of Sciences of Tunis, University of Tunis El Manar, Tunis 2092, Tunisia

,

Didier Dubreuil

^bUniversité de Nantes, CNRS, CEISAM, UMR 6230, 44000 Nantes, France

,

Hédi M’rabet∗

^aLaboratory of Selective Organic & Heterocyclic Synthesis and Biological Activity Evaluation (LR17ES01), Department of Chemistry, Faculty of Sciences of Tunis, University of Tunis El Manar, Tunis 2092, Tunisia

,

Jacques Lebreton

^bUniversité de Nantes, CNRS, CEISAM, UMR 6230, 44000 Nantes, France

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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

Key words

organophosphorus compounds - 1,3-dipolar cycloaddition - Heck coupling reaction - radical cyclization - metathesis

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