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An optimized procedure for direct access to 1H-indazole-3-carboxaldehyde derivatives by nitrosation of indoles

Arnaud Chevalier 1 Abdelaaziz Ouahrouch 1 Alexandre Arnaud 1 Thibault Gallavardin 1 Xavier Franck 1
1 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse
Abstract : Indazole derivatives are currently drawing more and more attention in medicinal chemistry as kinase inhibitors. 1H-indazole-3-carboxaldehydes are key intermediates to access to a variety of polyfunctionalized 3-substituted indazoles. We report here a general access to this motif, based on the nitrosation of indoles in a slightly acidic environment. These very mild conditions allow the conversion of both electron-rich and electron-deficient indoles into 1H-indazole-3-carboxaldehydes.
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https://hal-normandie-univ.archives-ouvertes.fr/hal-02024488
Contributor : Madeleine Roux-Merlin <>
Submitted on : Tuesday, February 19, 2019 - 11:09:21 AM
Last modification on : Thursday, July 2, 2020 - 3:29:49 AM

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Arnaud Chevalier, Abdelaaziz Ouahrouch, Alexandre Arnaud, Thibault Gallavardin, Xavier Franck. An optimized procedure for direct access to 1H-indazole-3-carboxaldehyde derivatives by nitrosation of indoles. RSC Advances, Royal Society of Chemistry, 2018, 8 (24), pp.13121-13128. ⟨10.1039/c8ra01546e⟩. ⟨hal-02024488⟩

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