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

Abstract : 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.
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https://hal-normandie-univ.archives-ouvertes.fr/hal-02899329
Contributor : Madeleine Roux-Merlin <>
Submitted on : Wednesday, July 15, 2020 - 9:36:57 AM
Last modification on : Thursday, July 16, 2020 - 3:49:52 AM

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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 and Biomolecular Chemistry, Royal Society of Chemistry, 2020, 18 (18), pp.3481-3486. ⟨10.1039/D0OB00582G⟩. ⟨hal-02899329⟩

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