Access to 1H-indazoles, 1H-benzoindazoles and 1H-azaindazoles from (het)aryl azides: a one-pot Staudinger-aza-Wittig reaction leading to N–N bond formation?

T. Alaime; M. Daniel; M.-A. Hiebel; E. Pasquinet; F. Suzenet; G. Guillaumet

doi:10.1039/C8CC03612H

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Access to 1H-indazoles, 1H-benzoindazoles and 1H-azaindazoles from (het)aryl azides: a one-pot Staudinger-aza-Wittig reaction leading to N–N bond formation?†

T. Alaime,‡^ab M. Daniel,‡^ab M.-A. Hiebel,^b E. Pasquinet,*^a F. Suzenet

*^b and G. Guillaumet^b

Author affiliations

* Corresponding authors

^a CEA, DAM, Le Ripault, F-37260 Monts, France
E-mail: eric.pasquinet@cea.fr

^b Institut de Chimie Organique et Analytique, Université d’Orléans, UMR-CNRS 7311, LRC CEA M09, 45067 Orléans, France
E-mail: franck.suzenet@univ-orleans.fr

Abstract

The synthesis of various substituted 1H-indazoles is reported through N–N bond formation from an iminophosphorane derivative. Supported by control experiments, an original Staudinger-aza-Wittig tandem mechanism is proposed for this transformation.

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Article information

DOI: https://doi.org/10.1039/C8CC03612H
Article type: Communication
Submitted: 04 May 2018
Accepted: 03 Jul 2018
First published: 04 Jul 2018

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Chem. Commun., 2018,54, 8411-8414

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Access to 1H-indazoles, 1H-benzoindazoles and 1H-azaindazoles from (het)aryl azides: a one-pot Staudinger-aza-Wittig reaction leading to N–N bond formation?

T. Alaime, M. Daniel, M.-A. Hiebel, E. Pasquinet, F. Suzenet and G. Guillaumet, Chem. Commun., 2018, 54, 8411 DOI: 10.1039/C8CC03612H

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Chemical Communications

Access to 1H-indazoles, 1H-benzoindazoles and 1H-azaindazoles from (het)aryl azides: a one-pot Staudinger-aza-Wittig reaction leading to N–N bond formation?†

Abstract

Supplementary files

Article information

Download Citation

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Access to 1H-indazoles, 1H-benzoindazoles and 1H-azaindazoles from (het)aryl azides: a one-pot Staudinger-aza-Wittig reaction leading to N–N bond formation?

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