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
a   Laboratory 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
b   Université de Nantes, CNRS, CEISAM, UMR 6230, 44000 Nantes, France
,
Virginie Blot
b   Université de Nantes, CNRS, CEISAM, UMR 6230, 44000 Nantes, France
,
Monique Mathé-Allainmat
b   Université de Nantes, CNRS, CEISAM, UMR 6230, 44000 Nantes, France
,
Mohamed Lotfi Efrit
a   Laboratory 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
b   Université de Nantes, CNRS, CEISAM, UMR 6230, 44000 Nantes, France
,
Hédi M’rabet
a   Laboratory 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
b   Université de Nantes, CNRS, CEISAM, UMR 6230, 44000 Nantes, France
› Author Affiliations
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.

Supporting Information



Publication History

Received: 21 November 2023

Accepted after revision: 05 January 2024

Article published online:
15 February 2024

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