57638-63-8Relevant academic research and scientific papers
One-Pot Asymmetric Oxidative Dearomatization of 2-Substituted Indoles by Merging Transition Metal Catalysis with Organocatalysis to Access C2-Tetrasubstituted Indolin-3-Ones
Zhao, Yong-Long,An, Jian-Xiong,Yang, Fen-Fen,Guan, Xiang,Fu, Xiao-Zhong,Li, Zong-Qin,Wang, Da-Peng,Zhou, Meng,Yang, Yuan-Yong,He, Bin
, p. 1277 - 1285 (2022/03/14)
A one-pot approach for the asymmetric synthesis of C2-tetrasubstituted indolin-3-ones from 2-substituted indoles was developed via merging transition metal catalysis with organocatalysis. This strategy involves two processes, including CuI catalyzed oxidative dearomatization of 2-substituted indoles using O2 as green oxidant, and followed by an proline-promoted asymmetric Mannich reaction with ketones or aldehydes. A series of C2-tetrasubstituted indolin-3-ones were obtained in 35–86% yields, 2:1->20:1 dr and 48–99% ee. Moreover, the synthetic 2-tetrasubstituted indolin-3-ones could be easily transformed into 1H-[1,3] oxazino [3,4-a]indol-5(3H)-ones via a [4+1] cyclization process. In addition, the synthetic compound 3 s show certain antibacterial activity against S. aureus ATCC25923 and multi-drug resistance bacterial strain of S. aureus (20151027077) and its MIC values up to 8 μg/mL and 16 μg/mL, respectively. (Figure presented.).
Cascade annulative π-extension for the rapid construction of carbazole based polyaromatic hydrocarbons
Banerjee, Ankush,Ghosh, Meghna,Kundu, Samrat,Maji, Modhu Sudan,Pal, Shyam Chand
supporting information, p. 5762 - 5765 (2021/06/16)
A Br?nsted acid catalyzed cascade benzannulation strategy for the one-pot synthesis of densely populated poly-aryl benzo[a]carbazole architectures is disclosed from easily affordable fundamental commodities. The efficacy of this technique was further validated via the concise synthesis of structurally unique carbazole based poly-aromatic hydrocarbons. Furthermore, the photo-physical properties of the synthesized compounds are thoroughly investigated.
Iminyl-radicals by electrochemical decarboxylation of α-imino-oxy acids: construction of indole-fused polycyclics
Wan, Jin-Lin,Cui, Jian-Feng,Zhong, Wei-Qiang,Huang, Jing-Mei
supporting information, p. 10242 - 10245 (2021/10/12)
Iminyl radicals are reactive intermediates that can be used for the construction of various valuable heterocycles. Herein, the electrochemical decarboxylation of α-imino-oxy acids for the generation of iminyl radicals has been accomplished under exogenous-oxidant- and metal-free conditions through the use ofnBu4NBr as a mediator. The resulting iminyl radicals undergo intramolecular cyclization smoothly with the adjacent (hetero)arenes to afford a series of indole-fused polycyclic compounds.
Well-defined (NHC)Pd(N–heterocyclic carboxylate)(OAc) complexes-catalyzed direct C2-arylation of free (NH)-indoles with arylsulfonyl hydrazides
Yang, Jin,Zong, Ling-Li,Zhu, Xiao-Ting,Zhu, Xin-Ying,Zhao, Jian-Yi
, (2020/08/24)
A series of well-defined (NHC)Pd(N–heterocyclic carboxylate)(OAc) complexes (N–heterocyclic carboxylate = pyridine-2-carboxylate, quinoline-2-carboxylate and isoquinoline-1-carboxylate) were synthesized and fully characterized by NMR spectra, HR-MS and X-ray single crystal diffraction. The obtained complexes were then used for direct C2-arylation of free (NH)-indoles with arylsulfonyl hydrazides. With low catalyst loading, all complexes exhibited high catalytic activities for the arylation reactions.
Synthesis of 2-substituted indole with Hantzsch ester catalyzed by palladium
Li, Yanan,Wang, Bo,Xing, Ruiguang
, p. 295 - 303 (2019/08/01)
An efficient reductive cyclization of o-nitrobenzyl ketone compounds was achieved by using a Hantzsch 1,4-dihydropyridine ester as a biomimetic reducing agent in the presence of catalytic palladium on carbon. 2-Substituted indoles were obtained in good yields. Investigation of the mechanism suggests that palladium hydride promotes the reduction of nitro group, and acetic acid was beneficial for the loss of water to produce the intended product. This reaction system can not only broaden the use of Hantzsch 1,4-dihydropyridine ester, but it also provides a novel approach for preparing indole compounds.
Regioselective Synthesis of 2-Arylindoles via Palladium-Catalyzed Cyclization of Phenylglyoxal and 2-Anilinoacetophenones with Anilines
Benitez-Medina, G. Eliad,Ortiz-Soto, Sofía,Cabrera, Armando,Amézquita-Valencia, Manuel
, p. 3763 - 3770 (2019/06/24)
A versatile route has been developed for the synthesis of 2-arylindoles using a Pd-catalyzed tandem process. Under reductive conditions, different 2-arylindoles were synthesized from phenylglyoxal and aniline. This synthetic methodology involves a tandem reaction of four steps with high regioselectivity. Alternatively, 2-anilinoacetophenones intermediates also can be using to give access to the corresponding 2-arylindoles.
Nickel-Catalyzed Intramolecular Direct Arylation of Imines toward Diverse Indoles
Long, Han,Xu, Kunhua,Chen, Shanshan,Lin, Jin,Wu, Dan,Wu, Bo,Tian, Xu,Ackermann, Lutz
supporting information, (2019/05/08)
An efficient nickel-catalyzed intramolecular direct arylation of imines with challenging aryl chlorides has been developed. The versatile nickel catalysis made use of easily accessible imines and delivered diversely decorated 2-arylindoles of considerable importance to biological and medicinal chemistry.
Nickel-Catalyzed Intramolecular Direct Arylation of Imines toward Diverse Indoles
Long, Han,Xu, Kunhua,Chen, Shanshan,Lin, Jin,Wu, Dan,Wu, Bo,Tian, Xu,Ackermann, Lutz
supporting information, p. 3053 - 3056 (2019/05/10)
An efficient nickel-catalyzed intramolecular direct arylation of imines with challenging aryl chlorides has been developed. The versatile nickel catalysis made use of easily accessible imines and delivered diversely decorated 2-arylindoles of considerable importance to biological and medicinal chemistry.
Palladium-catalyzed direct C2-arylation of free (N–H) indoles via norbornene-mediated regioselective C–H activation
Gao, Yadong,Zhu, Wangying,Yin, Long,Dong, Bo,Fu, Jingjing,Ye, Zhiwen,Xue, Fengtian,Jiang, Chao
supporting information, p. 2213 - 2216 (2017/05/16)
A palladium-catalyzed direct C2-arylation reaction of free (N–H) indoles has been developed. This reaction relies on a norbornene-mediated C–H activation process on the indole ring, which features high regioselectivity and excellent functional group tolerance.
Structure-activity relationships and docking studies of synthetic 2-arylindole derivatives determined with aromatase and quinone reductase 1
Prior, Allan M.,Yu, Xufen,Park, Eun-Jung,Kondratyuk, Tamara P.,Lin, Yan,Pezzuto, John M.,Sun, Dianqing
, p. 5393 - 5399 (2017/11/20)
In our ongoing effort of discovering anticancer and chemopreventive agents, a series of 2-arylindole derivatives were synthesized and evaluated toward aromatase and quinone reductase 1 (QR1). Biological evaluation revealed that several compounds (e.g., 2d, IC50 = 1.61 μM; 21, IC50 = 3.05 μM; and 27, IC50 = 3.34 μM) showed aromatase inhibitory activity with half maximal inhibitory concentration (IC50) values in the low micromolar concentrations. With regard to the QR1 induction activity, 11 exhibited the highest QR1 induction ratio (IR) with a low concentration to double activity (CD) value (IR = 8.34, CD = 2.75 μM), while 7 showed the most potent CD value of 1.12 μM. A dual acting compound 24 showed aromatase inhibition (IC50 = 9.00 μM) as well as QR1 induction (CD = 5.76 μM) activities. Computational docking studies using CDOCKER (Discovery Studio 3.5) provided insight in regard to the potential binding modes of 2-arylindoles within the aromatase active site. Predominantly, the 2-arylindoles preferred binding with the 2-aryl group toward a small hydrophobic pocket within the active site. The C-5 electron withdrawing group on indole was predicted to have an important role and formed a hydrogen bond with Ser478 (OH). Alternatively, meta-pyridyl analogs may orient with the pyridyl 3′-nitrogen coordinating with the heme group.
