54012-98-5Relevant academic research and scientific papers
Copper-catalyzed cascade C-N coupling/C-H amination: one pot synthesis of imidazo[1,2-b]indazole
Rajesham, Bandari,Arunkumar, Vemula,Naikawadi, Praveen Kumar,Shiva Kumar
, p. 15816 - 15820 (2020)
We report an efficient synthesis of imidazo[1,2-b]indazole starting from 2-(2H-indazol-2-yl)aniline with aryl/heteroaryl/aliphatic bromide. This novel transformation involves a one-pot Cu-catalyzed cascade process combining C-N coupling between 2-(2H-indazol-2-yl)aniline and aryl/heteroaryl/aliphatic bromide followed by intramolecular C-H amination to afford the desired compounds in good yields.
C(sp2)-H Functionalization of 2H-Indazoles at C3-Position via Palladium(II)-Catalyzed Isocyanide Insertion Strategy Leading to Diverse Heterocycles
Vidyacharan, Shinde,Murugan, Arumugavel,Sharada, Duddu S.
, p. 2837 - 2848 (2016/04/26)
Herein, we have reported an efficient Pd-catalyzed C-H functionalization of 2H-indazole at C3-position via an isocyanide insertion strategy for the synthesis of unprecedented benzoxazinoindazoles, indazoloquinaoxalines and benzoxazinoindazolones for the f
A facile synthesis of 2H-indazoles under neat conditions and further transformation into aza-γ-carboline alkaloid analogues in a tandem one-pot fashion
Vidyacharan, Shinde,Sagar,Chaitra,Sharada, Duddu S.
, p. 34232 - 34236 (2014/11/07)
We have described a facile, microwave-assisted, catalyst-free and solvent-free approach to 2H-indazoles and further developed a robust tandem one-pot metal-free strategy for C-C bond formation at the C-3 position of 2H-indazoles leading to a unique class
Copper-diamine-catalyzed N-arylation of pyrroles, pyrazoles, indazoles, imidazoles, and triazoles
Antilla, Jon C.,Baskin, Jeremy M.,Barder, Timothy E.,Buchwald, Stephen L.
, p. 5578 - 5587 (2007/10/03)
This paper details the copper-catalyzed N-arylation of π-excessive nitrogen heterocycles. The coupling of either aryl iodides or aryl bromides with common nitrogen heterocycles (pyrroles, pyrazoles, indazoles, imidazoles, and triazoles) was successfully performed in good yield with catalysts derived from diamine ligands and CuI. General conditions were found that tolerate functional groups such as aldehydes, ketones, alcohols, primary amines, and nitriles on the aryl halide or heterocycle. Hindered aryl halides or heterocycles were also found to be suitable substrates using the conditions reported herein.
1H- and 2H-Indazoles by Thermal and Photolytic Decomposition of o-Azidobenzoic Acid and o-Azidobenzaldehyde Derivatives
Ardakani, Manouchehr Azadi,Smalley, Robert K.,Smith, Richard H.
, p. 2501 - 2506 (2007/10/02)
Ethyl o-azidobenzimidate (6) and o-azidobenzamidine (7) on thermolysis yield 3-ethoxy- (9; X=OEt) and 3-amino-1H-indazole (9; X=NH2), respectively.The former product is also obtained on irradiation of the imidate in methanol-tetrahydrofuran solution. 2-Aryl- and 2-heteroaryl-3-chloro-2H-indazoles have been prepared by the action of hot thionyl chloride on o-azidoanilides.The trichloro-2H-indazoles obtained by the action of phosphorus pentachloride on o-azidobenzanilide (12) and by the action of thionyl chloride on N-(o-azidobenzoyl)-2-aminopyridine have been identified as the 3,5,7-trichloro derivatives.The reductive dehalogenation, nitration, and reactivity of the halogen towards nucleophiles, of 3-chloro-2-phenyl-2H-indazole (19) are reported.A new practicable synthesis of o-azidobenzaldehyde (31; X=O) is described.Thermolysis of its phenylhydrazone and semicarbazone derivatives yields 2H-indazoles.
