ArticleJournal of the American Chemical Society2019
Accessing Multiple Classes of 2 H-Indazoles: Mechanistic Implications for the Cadogan and Davis-Beirut Reactions.
Article in Journal of the American Chemical Society, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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Who cites it
9 citing papers in PubMed, 32 citations in OpenAlex.
- Probing 3-Amino-2H-Azaindazoles as Allosteric Inhibitors of the Protein Tyrosine Phosphatase SHP2.ChemMedChem · 2026Article
- Mo-Catalyzed One-Pot Synthesis of N-Polyheterocycles from Nitroarenes and Glycols with Recycling of the Waste Reduction Byproduct. Substituent-Tuned Photophysical Properties.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
- Direct Preparation ofThe Journal of organic chemistry · 2021Article
- Davis-Beirut Reaction Inspired Nitroso Diels-Alder Reaction.Tetrahedron letters · 2021Article
- Towards Knowledge Maintenance in Scientific Digital Libraries with the Keystone Framework.Proceedings of the ... ACM/IEEE Joint Conference on Digital Libraries. ACM/IEEE Joint Conference on Digital Libraries · 2020Article
- An Improved PJournal of the American Chemical Society · 2020Article
- Characterization of Leptazolines A-D, Polar Oxazolines from the CyanobacteriumOrganic letters · 2019Article
- Davis-Beirut Reaction: Diverse Chemistries of Highly Reactive Nitroso Intermediates in Heterocycle Synthesis.Accounts of chemical research · 2019Review
- Davis-Beirut Reaction: A Photochemical Brønsted Acid Catalyzed Route toOrganic letters · 2019Article
Corrections and comments
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Authors and funding
8 authors at 2 institutions in 2 countries.
Funding
Abstract
The Cadogan cyclization is a robust but harsh method for the synthesis of 2 H-indazoles, a valuable class of nitrogen heterocycles. Although nitrene generation by exhaustive deoxygenation is widely accepted as the operating mechanism in the reductive cyclization of nitroaromatics, non-nitrene pathways have only been theorized previously. Here, 2 H-indazole N-oxides were synthesized through an interrupted Cadogan/Davis-Beirut reaction and are presented as direct evidence of competent oxygenated intermediates; mechanistic implications for both reactions are discussed. Isolation and characterization of these N-oxides enabled a formal Cadogan cyclization at room temperature for 2 H-indazole synthesis.
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