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Communication Dans Un Congrès Année : 2023

Study and development of polar organometallic tools: synthesis of fused (hetero)aryl lactones

Résumé

Phthalides and derivatives are widespread in biologically active compounds and natural products. These heterocycles can also serve as versatile building blocks for the synthesis of natural and pharmaceutically-important products. Their preparation is widely documented in the literature even though many of their synthetic routes are non-convergent and relied on intramolecular cyclization, requiring relatively complex syntheses of the starting materials in order to bring diversity to the final phthalides. Moreover, fused heteroaryl-lactones (pyridinyland benzothienyl-) are poorly exemplified in the literature. In the past few years, our laboratory has been focusing on developing chemistry using bimetallic ate complexes composed of a polar organometallic and a “soft” organometallic in metal halogen exchange (MHE) reaction. Based on that expertise, we decided to started a research program with the aim of exploring the reactivity of organomagnesiates for the synthesis of substituted phthalides, azaphthalides and also fused benzothienyl-lactones. Thereby, we showed that BIPHEN or BINOL-based monobutylmagnesiate ((rac)- BIPHENBuMgLi or (rac)-BINOLBuMgLi) can efficiently promote the MHE of easily available 2-iodobenzoate derivatives, followed by addition of an aldehyde or a ketone which lead to an intramolecular cyclisation, and the formation of a series of new diversely substituted phthalide derivatives in moderate to good yield.

Domaines

Chimie
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Dates et versions

hal-04411370 , version 1 (23-01-2024)

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Copyright (Tous droits réservés)

Identifiants

  • HAL Id : hal-04411370 , version 1

Citer

Sabrina Touchet, Lynda Hammas, Callum Yeardley, Charles T. O'Hara, Corinne Comoy, et al.. Study and development of polar organometallic tools: synthesis of fused (hetero)aryl lactones. Journée d'Automne 2023, Division de Chimie Organique - Société Chimique de France (DCO - SCF), Dec 2023, Paris, France. ⟨hal-04411370⟩
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