329220-10-2Relevant academic research and scientific papers
Synthesis of 3-aryl/heteroaryl-1-methyl-1H-indazoles and evaluation of their biological activities
Mohan, Arasavelli Ananda,Sharma, Ganapavarapu V. R.,Vidavalur, Siddaiah
, p. 287 - 294 (2018/09/14)
The synthesis of 3-aryl/heteroaryl-1-methyl-1H-indazole derivatives (5a-j) was achieved from commercially available 1H-indazole through the Suzuki cross-coupling reaction. The indazoles 5a-j were synthesized through two alternative routes (Route 1 and Route 2) from the same starting material and characterized using1H nuclear magnetic resonance (NMR),13C NMR, infrared, and liquid chromatography-mass spectrometry data. The first step which is common step to both routes involves conversion of 1H-3-iodo-1H-indazole (2). The antibacterial activity of 5a-j and intermediates 3a-j was evaluated against two Gram-positive and two Gram-negative bacterial strains and anticancer activity against HT-29 and MDA-MB-231cancer cell lines.
A Synthesis of 1H-Indazoles via a Cu(OAc)2-Catalyzed N-N Bond Formation
Chen, Cheng-Yi,Tang, Guangrong,He, Fengxian,Wang, Zhaobin,Jing, Hailin,Faessler, Roger
supporting information, p. 1690 - 1693 (2016/04/26)
A facile synthesis of 1H-indazoles featuring a Cu(OAc)2-catalyzed N-N bond formation using oxygen as the terminal oxidant is described. The reaction of readily available 2-aminobenzonitriles with various organometallic reagents led to o-aminoar
A robust protocol for Pd(ii)-catalyzed C-3 arylation of (1H) indazoles and pyrazoles: Total synthesis of nigellidine hydrobromide
Ye, Mengchun,Edmunds, Andrew J.F.,Morris, James A.,Sale, David,Zhang, Yejia,Yu, Jin-Quan
, p. 2374 - 2379 (2013/07/25)
C3-arylated indazole and pyrazoles are privileged structural motifs in agrochemicals and pharmaceuticals. C-3 C-H arylation of (1H) indazole and pyrazole has been a significant challenge due to the poor reactivity of the C-3 position. Herein, we report a practical Pd(ii)/Phen catalyst and conditions for the direct C-3 arylation of indazole and pyrazole with ArI or ArBr without using Ag additives as halide scavengers. The use of toluene, chlorobenzene, trifluoromethylbenzene and mesitylene as the solvent was found to be crucial for the selectivity and reactivity. We further demonstrate the robustness of this protocol through the first total synthesis of nigellidine hydrobromide as well as the expedient preparation of heterocycles structurally related to pesticides and drug molecules.
