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

Maxime Manneveau | Zendy; Saori Tanii | Zendy; Fanny Gens | Zendy; Julien Legros | Zendy; Isabelle Chataigner | Zendy

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

Author(s) -

Maxime Manneveau,

Saori Tanii,

Fanny Gens,

Julien Legros,

Isabelle Chataigner

Publication year - 2020

Publication title -

organic and biomolecular chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.923

H-Index - 146

eISSN - 1477-0539

pISSN - 1477-0520

DOI - 10.1039/d0ob00582g

Subject(s) - cycloaddition , flow chemistry , chemistry , flow (mathematics) , organic chemistry , combinatorial chemistry , polymer science , mathematics , catalysis , geometry

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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