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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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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Abstract 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.
AbstractList 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.
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 2 -indazoles which are frequently used in drug design, and we also demonstrated its applicability to less studied 3 -indazoles.
Author Covini, David
Bitai, Jacqueline
Dank, Christian
Karolyi-Oezguer, Jale
Gollner, Andreas
Schoeggl Toledano, Anna
Berger, Helmut
AuthorAffiliation Boehringer Ingelheim RCV GmbH & Co KG
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  givenname: Anna
  surname: Schoeggl Toledano
  fullname: Schoeggl Toledano, Anna
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  givenname: Jacqueline
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  orcidid: 0000-0002-4347-8296
  surname: Gollner
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  email: a_gollner@hotmail.com
BackLink https://www.ncbi.nlm.nih.gov/pubmed/38315455$$D View this record in MEDLINE/PubMed
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Keywords REGIOSELECTIVE SYNTHESIS
CONDENSATION
3-COMPONENT SYNTHESIS
2H-INDAZOLES
ONE-POT
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Snippet Herein we report a method for the synthesis of indazoles from readily available 2-aminomethyl-phenylamines via N–N bond-forming oxidative cyclization. Inspired...
Herein we report a method for the synthesis of indazoles from readily available 2-aminomethyl-phenylamines via N-N bond-forming oxidative cyclization. Inspired...
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StartPage 1229
SubjectTerms Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
Title Synthesis of Indazoles via N–N Bond-Forming Oxidative Cyclization from 2‑Aminomethyl-phenylamines
URI http://dx.doi.org/10.1021/acs.orglett.4c00036
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https://www.ncbi.nlm.nih.gov/pubmed/38315455
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Volume 26
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