Novel strategy for the preparation of 3-perfluoroalkylated-2H-indazole derivatives

Hassen Bel Abed; Nils Weißing; Jens Schoene; Jannik Paulus; Norbert Sewald; Marc Nazaré

doi:10.1016/j.tetlet.2018.03.051

Novel strategy for the preparation of 3-perfluoroalkylated-2H-indazole derivatives

Hassen Bel Abed, Nils Weißing, Jens Schoene, Jannik Paulus, Norbert Sewald, Marc Nazaré

Research output: Contribution to Journal › Article › Academic › peer-review

Abstract

A simple and novel methodology for the synthesis of 3-perfluoroalkylated-2H-indazole derivatives has been elaborated. The perfluoroalkylation of readily available 2-nitrobenzaldimines bearing electron donating groups was performed using the Ruppert-Prakash reagent and its analogues to afford α-difluoromethylated, α-trifluoromethylated and α-pentafluoroethylated benzylamines. A final reductive cyclization mediated by SnCl2·2H2O led to 2H-indazoles containing perfluoroalkyl groups via the generation of a new N–N bond in moderate to good yields.

Original language	English
Pages (from-to)	1813-1815
Journal	Tetrahedron Letters
Volume	59
Issue number	19
DOIs	https://doi.org/10.1016/j.tetlet.2018.03.051
Publication status	Published - 9 May 2018
Externally published	Yes

Funding

This Letter is dedicated to Mongi Bel Abed, an exceptional father (10/08/1951-16/01/2017). The authors thank Edgar Specker for recording the HRMS spectra, Peter Schmieder and Nils Trieloff for NMR assistance. We thank the Berlin Institute of Health (BIH) and the Helmholtz Drug Research for financial support.

Funders	Funder number
Helmholtz Drug Research
Berlin Institute of Health

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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abstract = "A simple and novel methodology for the synthesis of 3-perfluoroalkylated-2H-indazole derivatives has been elaborated. The perfluoroalkylation of readily available 2-nitrobenzaldimines bearing electron donating groups was performed using the Ruppert-Prakash reagent and its analogues to afford α-difluoromethylated, α-trifluoromethylated and α-pentafluoroethylated benzylamines. A final reductive cyclization mediated by SnCl2·2H2O led to 2H-indazoles containing perfluoroalkyl groups via the generation of a new N–N bond in moderate to good yields.",

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AU - Bel Abed, Hassen

AU - Weißing, Nils

AU - Schoene, Jens

AU - Paulus, Jannik

AU - Sewald, Norbert

AU - Nazaré, Marc

PY - 2018/5/9

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AB - A simple and novel methodology for the synthesis of 3-perfluoroalkylated-2H-indazole derivatives has been elaborated. The perfluoroalkylation of readily available 2-nitrobenzaldimines bearing electron donating groups was performed using the Ruppert-Prakash reagent and its analogues to afford α-difluoromethylated, α-trifluoromethylated and α-pentafluoroethylated benzylamines. A final reductive cyclization mediated by SnCl2·2H2O led to 2H-indazoles containing perfluoroalkyl groups via the generation of a new N–N bond in moderate to good yields.

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 19

ER -

Novel strategy for the preparation of 3-perfluoroalkylated-2H-indazole derivatives

Abstract

Funding

UN SDGs

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