volume 26 issue 6 pages 1229-1232

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

Anna Schoeggl Toledano 1
Jacqueline Bitai 1
David Covini 1
Jale Karolyi-Oezguer 1
Christian Dank 1
Helmut Berger 1
Andreas Gollner 1
1
 
Boehringer Ingelheim RCV GmbH & Co KG, Dr. Boehringer-Gasse 5-11, A-1121 Vienna, Austria
Publication typeJournal Article
Publication date2024-02-05
scimago Q1
wos Q1
SJR1.235
CiteScore8.7
Impact factor5.0
ISSN15237060, 15237052
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
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.
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GOST Copy
Schoeggl Toledano A. et al. Synthesis of Indazoles via N–N Bond-Forming Oxidative Cyclization from 2-Aminomethyl-phenylamines // Organic Letters. 2024. Vol. 26. No. 6. pp. 1229-1232.
GOST all authors (up to 50) Copy
Schoeggl Toledano A., Bitai J., Covini D., Karolyi-Oezguer J., Dank C., Berger H., Gollner A. Synthesis of Indazoles via N–N Bond-Forming Oxidative Cyclization from 2-Aminomethyl-phenylamines // Organic Letters. 2024. Vol. 26. No. 6. pp. 1229-1232.
RIS |
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RIS Copy
TY - JOUR
DO - 10.1021/acs.orglett.4c00036
UR - https://pubs.acs.org/doi/10.1021/acs.orglett.4c00036
TI - Synthesis of Indazoles via N–N Bond-Forming Oxidative Cyclization from 2-Aminomethyl-phenylamines
T2 - Organic Letters
AU - Schoeggl Toledano, Anna
AU - Bitai, Jacqueline
AU - Covini, David
AU - Karolyi-Oezguer, Jale
AU - Dank, Christian
AU - Berger, Helmut
AU - Gollner, Andreas
PY - 2024
DA - 2024/02/05
PB - American Chemical Society (ACS)
SP - 1229-1232
IS - 6
VL - 26
PMID - 38315455
SN - 1523-7060
SN - 1523-7052
ER -
BibTex |
Cite this
BibTex (up to 50 authors) Copy
@article{2024_Schoeggl Toledano,
author = {Anna Schoeggl Toledano and Jacqueline Bitai and David Covini and Jale Karolyi-Oezguer and Christian Dank and Helmut Berger and Andreas Gollner},
title = {Synthesis of Indazoles via N–N Bond-Forming Oxidative Cyclization from 2-Aminomethyl-phenylamines},
journal = {Organic Letters},
year = {2024},
volume = {26},
publisher = {American Chemical Society (ACS)},
month = {feb},
url = {https://pubs.acs.org/doi/10.1021/acs.orglett.4c00036},
number = {6},
pages = {1229--1232},
doi = {10.1021/acs.orglett.4c00036}
}
MLA
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MLA Copy
Schoeggl Toledano, Anna, et al. “Synthesis of Indazoles via N–N Bond-Forming Oxidative Cyclization from 2-Aminomethyl-phenylamines.” Organic Letters, vol. 26, no. 6, Feb. 2024, pp. 1229-1232. https://pubs.acs.org/doi/10.1021/acs.orglett.4c00036.