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Article Dans Une Revue Organic & Biomolecular Chemistry Année : 2020

Dearomatization of 3-cyanoindoles by (3 + 2) cycloaddition: from batch to flow chemistry

Résumé

1,3-Dipolar dearomatizing cycloadditions between a non-stabilized azomethine ylide and 3-cyanoindoles or benzofuran afford the corresponding 3D-heterocycles bearing a quaternary carbon centre at the ring junction. While 6 equivalents of ylide precursor 1 are required for full conversion in a classical flask, working under flow conditions limits the excess (3 equiv., tR = 1 min) and leads to a cleaner process, affording cycloadducts that are easier to isolate.

Domaines

Chimie organique
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Dates et versions

hal-02996918 , version 1 (11-11-2020)

Identifiants

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Maxime Manneveau, Saori Tanii, Fanny Gens, Julien Legros, Isabelle Chataigner. Dearomatization of 3-cyanoindoles by (3 + 2) cycloaddition: from batch to flow chemistry. Organic & Biomolecular Chemistry, 2020, 18 (18), pp.3481-3486. ⟨10.1039/d0ob00582g⟩. ⟨hal-02996918⟩
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