17049-65-9Relevant academic research and scientific papers
A B2(OH)4-Mediated Synthesis of 2-Substituted Indazolone and Its Application in a DNA-Encoded Library
Bao, Yapeng,Deng, Zongfa,Feng, Jing,Zhu, Weiwei,Li, Jin,Wan, Jinqiao,Liu, Guansai
supporting information, p. 6277 - 6282 (2020/08/24)
Indazolone cores are among the most common structural components in medicinal chemistry and can be found in many biologically active molecules. In this report, a mild and efficient approach to 2-substituted indazolones via B2(OH)4-mediated reductive N-N b
Davis-Beirut Reaction: A Photochemical Br?nsted Acid Catalyzed Route to N-Aryl 2 H-Indazoles
Kraemer, Niklas,Li, Clarabella J.,Zhu, Jie S.,Larach, Julio M.,Tsui, Ka Yi,Tantillo, Dean J.,Haddadin, Makhluf J.,Kurth, Mark J.
supporting information, p. 6058 - 6062 (2019/08/20)
The Davis-Beirut reaction provides access to 2H-indazoles from aromatic nitro compounds. However, N-aryl targets have been traditionally challenging to access due to competitive alternate reaction pathways. Previously, the key nitroso imine intermediate w
N-N Bond Formation between Primary Amines and Nitrosos: Direct Synthesis of 2-Substituted Indazolones with Mechanistic Insights
Zhu, Jie S.,Kraemer, Niklas,Shatskikh, Marina E.,Li, Clarabella J.,Son, Jung-Ho,Haddadin, Makhluf J.,Tantillo, Dean J.,Kurth, Mark J.
supporting information, p. 4736 - 4739 (2018/08/24)
A concise, one-step route to indazolones from primary alkyl amines and o-nitrobenzyl alcohols is reported. The key step in this readily scalable indazolone forming process involves base-mediated in situ o-nitrobenzyl alcohol → o-nitrosobenzaldehyde conversion. Although this functional group interconversion is known to be useful for 2H-indazole synthesis, its reactivity was modulated for indazolone formation.
Palladium-Catalyzed Carbonylative Cyclization of Azoarenes
Wang, Zechao,Yin, Zhiping,Zhu, Fengxiang,Li, Yahui,Wu, Xiao-Feng
, p. 3637 - 3640 (2017/10/13)
In this communication, we established an interesting palladium-catalyzed carbonylation protocol for the intramolecular cyclization of azoarenes. With Mo(CO)6 as the solid CO source and through C(sp2)?H bond activation, a series of azoarenes were transformed into the corresponding 2-arylindazolones in moderate to good yields. Notably, not only symmetrical azoarenes, but also unsymmetrical substrates underwent the reaction with excellent regioselectivity.
Method for synthesis of indazolone compound
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Paragraph 0034; 0035; 0036, (2017/09/01)
The invention provides a novel method for synthesis of an indazolone compound. The method comprises that an alkali is added into o-halogenated aromatic formylhydrazine as a raw material, and the mixture is heated in a solvent so that a 1-aryl and 2-aryl indazolone compound having a high yield is obtained. The method is free of a transition metal catalyst, is simple in operation, has a high reaction yield and has a very high practical value in industrial preparation of the indazolone compound.
A Convenient Synthesis of 1-Aryl- A nd 2-Aryl-Substituted Indazolones via Intramolecular C-N Coupling Promoted by KO t-Bu
Wang, Wei-Juan,Chen, Jia-Hua,Chen, Zi-Cong,Zeng, Yu-Feng,Zhang, Xue-Jing,Yan, Ming,Chan, Albert S. C.
, p. 3551 - 3558 (2016/10/18)
A new method for the synthesis of 1-arylindazolones and 2-arylindazolones from N′-aryl-2-halobenzohydrazides promoted by KOt-Bu was developed. The difference of 2-halogen substituent exerted a significant effect on the distribution of the products. Two di
Potent, selective, and orally available benzoisothiazolone phosphomannose isomerase inhibitors as probes for congenital disorder of glycosylation Ia
Dahl, Russell,Bravo, Yalda,Sharma, Vandana,Ichikawa, Mie,Dhanya, Raveendra-Panickar,Hedrick, Michael,Brown, Brock,Rascon, Justin,Vicchiarelli, Michael,Mangravita-Novo, Arianna,Yang, Li,Stonich, Derek,Su, Ying,Smith, Layton H.,Sergienko, Eduard,Freeze, Hudson H.,Cosford, Nicholas D. P.
experimental part, p. 3661 - 3668 (2011/06/27)
We report the discovery and validation of a series of benzoisothiazolones as potent inhibitors of phosphomannose isomerase (PMI), an enzyme that converts mannose-6-phosphate (Man-6-P) into fructose-6-phosphate (Fru-6-P) and, more importantly, competes wit
On the illusive nature of o-formylazobenzenes: Exploiting the nucleophilicity of the azo group for cyclization to indazole derivatives
Peters, Maike V.,Stoll, Ragnar S.,Goddard, Richard,Buth, Gernot,Hecht, Stefan
, p. 7840 - 7845 (2007/10/03)
(Chemical Equation Presented) Facile rearrangement of azobenzenes is shown to occur in cases where the azo group is placed in the ortho position to carbonyl electrophiles to furnish the indazole skeleton. While this study demonstrates the illusive nature
Reactions of Azoarenes with Tributyltin Hydride
Alberti, Angelo,Bedogni, Nicola,Benaglia, Massimo,Leardini, Rino,Nanni, Daniele,et al.
, p. 607 - 613 (2007/10/02)
Tributyltin hydride when reacted with a series of substituted azoarenes afforded hydrazo compounds with high chemoselectivity and good to high yields.With ortho-substituted azoarenes, mixtures of hydrazo derivatives and N-heterocycles or cyclic products only were obtained.The kinetic law of the process was determined in the presence and in the absence of AIBN; with the radical initiator the reaction proceeds via a radical chain mechanism, whereas without AIBN the presence of stannyl free radicals could be discarded.The mechanism of the noninitiated reaction is discussed.EPR characterization of spin adducts obtained by reacting group IVB organometallic radicals with azo compounds is reported.
A convenient synthesis of 2-arylindazol-3-ones
Bird,Chng,Rama,Saeed
, p. 545 - 548 (2007/10/02)
The reductive cyclisation of o-nitrobenzanilides with zinc and sodium hydroxide in aqueous methanol provides a convenient source of 2-arylindazol-3-ones.
