Synthesis of Indazoles via N–N Bond-Forming Oxidative Cyclization from 2‑Aminomethyl-phenylamines

Herein we report a method for the synthesis of indazoles from readily available 2-aminomethyl-phenylamines via N–N bond-forming oxidative cyclization. Inspired by indazole formation initially observed as a side product by N. Coskun et al. we developed a robust protocol to access indazoles in all thr...

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Bibliographic Details
Published inOrganic letters Vol. 26; no. 6; pp. 1229 - 1232
Main Authors Schoeggl Toledano, Anna, Bitai, Jacqueline, Covini, David, Karolyi-Oezguer, Jale, Dank, Christian, Berger, Helmut, Gollner, Andreas
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 16.02.2024
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
REGIOSELECTIVE SYNTHESIS
CONDENSATION
3-COMPONENT SYNTHESIS
2H-INDAZOLES
ONE-POT
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Summary:Herein we report a method for the synthesis of indazoles from readily available 2-aminomethyl-phenylamines via N–N bond-forming oxidative cyclization. Inspired by indazole formation initially observed as a side product by N. Coskun et al. we developed a robust protocol to access indazoles in all three tautomeric forms. The method selectively gives access to various 2-substituted 2H-indazoles which are frequently used in drug design, and we also demonstrated its applicability to less studied 3H-indazoles.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.4c00036