- Ir(iii)-Catalysed electrooxidative intramolecular dehydrogenative C-H/N-H coupling for the synthesis of N-H indoles
-
Herein, an iridium(iii)-catalysed electrooxidative intramolecular dehydrogenative C-H/N-H coupling of unprotected 2-alkenyl anilines is described. The developed method allows the synthesis of a variety of 3-substituted N-H indole scaffolds under undivided electrolytic conditions. Mechanistic studies suggest that the reaction proceeds through the electro-oxidation induced reductive elimination pathway.
- Chang, Sukbok,Kim, Dongwook,Kim, Youyoung
-
p. 12309 - 12312
(2021/12/07)
-
- Electro-Oxidative C-N Bond Formation through Azolation of Indole Derivatives: An Access to 3-Substituent-2-(Azol-1-yl)indoles
-
A practical protocol to synthesize 3-substituent-2-(azol-1-yl)indole derivatives has been developed via an electrochemical oxidative cross coupling process under mild conditions. This electro-oxidative C-N bond formation strategy tolerates a range of functional groups and is amenable to gram scale synthesis. Moreover, this method was applied to the late-stage functionalization of bioactive molecules.
- Zhou, Naifu,Zhao, Junhao,Sun, Chengbo,Lai, Yuqin,Ruan, Zhixiong,Feng, Pengju
-
p. 16059 - 16067
(2021/10/01)
-
- Tandem Olefin Isomerization/Cyclization Catalyzed by Complex Nickel Hydride and Br?nsted Acid
-
We disclose a nickel/Br?nsted acid-catalyzed tandem process consisting of double bond isomerization of allyl ethers and amines and subsequent intramolecular reaction with nucleophiles. The process is accomplished by [(Me3P)4NiH]N(SO2CF3)2 in the presence of triflic acid. The methodology provides rapid access to tetrahydropyran-fused indoles and other oxacyclic scaffolds under very low catalyst loadings.
- Kathe, Prasad M.,Caciuleanu, Alexandru,Berkefeld, Andreas,Fleischer, Ivana
-
p. 15183 - 15196
(2020/11/30)
-
- Metal-free and regiospecific synthesis of 3-arylindoles
-
A convenient, metal-free, and organic acid-base promoted synthetic method to prepare 3-arylindoles from 3-aryloxirane-2-carbonitriles and arylhydrazine hydrochlorides has been developed. In the reaction, the organic acid catalyzes a tandem nucleophilic ri
- Xie, Wenlai,Xu, Chuangchuang,Xu, Jiaxi
-
p. 2661 - 2671
(2020/04/17)
-
- Regiospecificity in Ligand-Free Pd-Catalyzed C-H Arylation of Indoles: LiHMDS as Base and Transient Directing Group
-
A highly efficient catalyst-base pair for the C-H arylation of free (NH)-indoles in the C-3 position is reported. Ligand-free palladium acetate coupled with lithium hexamethyldisilazide (LiHMDS) catalyzed the regiospecific, i.e. 100% regioselective, C-3 a
- Camp, Clément,Canivet, Jér?me,Clot, Eric,Demarcy, Clément,Mohr, Yorck,Quadrelli, Elsje Alessandra,Renom-Carrasco, Marc,Thieuleux, Chloé,Wisser, Florian M.
-
p. 2713 - 2719
(2020/03/11)
-
- Heterocyclic com pounds and organic light-emitting diode including the same
-
The present invention relates to a novel heterocyclic compound and an organic electroluminescent device comprising the same. The heterocyclic compound is represented by the following Chemical Formula 1, and the organic electroluminescent device including the heterocyclic compound has excellent driving voltage, luminous efficiency, and lifespan properties. Chemical Formula 1. (by machine translation)
- -
-
Paragraph 0650-0656; 0676-0682
(2021/01/29)
-
- Design, synthesis and biological evaluation of novel indole derivatives as potential HDAC/BRD4 dual inhibitors and anti-leukemia agents
-
HDAC inhibitors and BRD4 inhibitors were considered to be potent anti-cancer agents. Recent studies have demonstrated that HDAC and BRD4 participate in the regulation of some signal paths like PI3K-AKT. In this work, a series of indole derivatives that co
- Cheng, Gaoliang,Wang, Zhi,Yang, Jinyu,Bao, Yu,Xu, Qihao,Zhao, Linxiang,Liu, Dan
-
p. 410 - 417
(2019/01/03)
-
- Photoredox Cyanomethylation of Indoles: Catalyst Modification and Mechanism
-
The direct cyanomethylation of indoles at the 2- or 3-position was achieved via photoredox catalysis. The versatile nitrile synthon is introduced as a radical generated from bromoacetonitrile, a photocatalyst, and blue LED as a light source. The mechanism of the reaction is explored by determination of the Stern-Volmer quenching constants. By combining photophysical data and mass spectrometry to follow the catalyst decomposition, the catalyst ligands were tuned to enable synthetically useful yields of radical coupling products. A range of indole substrates with alkyl, aryl, halogen, ester, and ether functional groups participate in the reaction, affording products in 16-90% yields. The reaction allows the rapid construction of synthetically useful cyanomethylindoles, products that otherwise require several synthetic steps.
- O'Brien, Connor J.,Droege, Daniel G.,Jiu, Alexander Y.,Gandhi, Shivaani S.,Paras, Nick A.,Olson, Steven H.,Conrad, Jay
-
p. 8926 - 8935
(2018/07/05)
-
- Discovery and evaluation of 3,5-disubstituted indole derivatives as Pim kinase inhibitors
-
Pim kinases are promising therapeutic targets for the treatment of hematological cancers. A potent Pim kinase inhibitor 7f, derived from meridianin C, was further optimized by the replacement of 2-aminopyrimidine with substituted benzene. The optimization of the C-3 and C-5 positions of indole yielded compound 43 with improved cellular potency and high selectivity against a panel of 14 different kinases.
- More, Kunal N.,Hong, Victor S.,Lee, Ahyeon,Park, Jongsung,Kim, Shin,Lee, Jinho
-
p. 2513 - 2517
(2018/06/06)
-
- Indole hydroxamic acid compounds with anti-tumor activity and application of compounds
-
The invention belongs to the technical field of medicines and relates to indole hydroxamic acid compounds with anti-tumor activity, in particular to hydroxamic acid compounds containing 1,3,5-trisubstituted indole, pharmaceutically accepted salt and hydra
- -
-
Paragraph 0045; 0049-0051
(2019/01/16)
-
- Pyridylmethylamine–Palladium Catalytic Systems: A Selective Alternative in the C?H Arylation of Indole
-
A highly efficient pyridylmethylamine-Pd alternative catalytic system for the C?H arylation of indole was explored. Variously substituted aryl groups were regio- and chemoselectively installed at the indole nucleus by using barium hydroxide as the base. The method was found to be efficient even in the presence of hindered coupling partners and Pd-reactive bonds.
- Perato, Serge,Large, Benjamin,Lu, Qiao,Gaucher, Anne,Prim, Damien
-
p. 389 - 392
(2017/02/15)
-
- Copper-mediated intramolecular aza-Wacker-type cyclization of 2-alkenylanilines toward 3-aryl indoles
-
A copper-mediated intramolecular aza-Wacker-type cyclization was developed for the direct and efficient synthesis of 3-aryl indoles using 2-alkenylanilines in moderate to good yields with good functional group compatibility. This strategy shows the high efficiency, operational simplicity as well as broad substrate scope.
- Yang, Rui,Yu, Jin-Tao,Sun, Song,Zheng, Qingheng,Cheng, Jiang
-
supporting information
p. 445 - 448
(2017/01/11)
-
- Water-medium C-H activation over a hydrophobic perfluoroalkane-decorated metal-organic framework platform
-
The use of water as reaction medium in the heterogeneous activation of C-H bonds has numerous advantages in terms of environmental benign, safety and cost efficiency impact. However, it is severely hampered because the reactants are difficult to dissolve in water and contact with the active sites of heterogeneous catalysts. Herein, we choose perfluoroalkane-functionalized mesoporous metal-organic framework (MOF) NU-1000 as a hydrophobic platform to encapsulate ultrafine palladium nanoparticles (Pd NPs) for C-H activation in water. The resultant Pd NPs stabilized by the perfluoroalkane exhibited high activity and regioselectivity in the direct C-H arylation of indoles in water. The introduction of perfluoroalkane chains into the mesoporous pores of NU-1000 provides hydrophobic surfaces to facilitate access of the reactants to the active sites to guarantee the high activity.
- Huang, Yuan-Biao,Shen, Min,Wang, Xusheng,Huang, Ping,Chen, Ruiping,Lin, Zu-Jin,Cao, Rong
-
-
- Indium-catalyzed annulation of 3-aryl- and 3-heteroarylindoles with propargyl ethers: Synthesis and photoluminescent properties of aryl- and heteroaryl[c]carbazoles
-
Treatment of 3-aryl- and 3-heteroarylindoles with propargyl ethers under indium catalysis successfully provided aryl- and heteroaryl[c]carbazoles, which were found to be more efficient emitters compared with the corresponding [a]-analogs.
- Nagase, Yuta,Shirai, Hiroyuki,Kaneko, Masayoshi,Shirakawa, Eiji,Tsuchimoto, Teruhisa
-
supporting information
p. 1456 - 1459
(2013/05/08)
-
- A tandem isomerization/prins strategy: Iridium(III)/Bronsted acid cooperative catalysis
-
Working together: A mild and efficient isomerization/protonation sequence generates pyran-fused indoles by cooperative catalysis between cationic iridium(III) and Bi(OTf)3. Three distinct cyclization manifolds lead to the corresponding bioactive scaffolds in good yields. In addition, N-substituted indoles can be synthesized enantioselectively in the presence of a chiral phosphate. Copyright
- Lombardo, Vince M.,Thomas, Christopher D.,Scheidt, Karl A.
-
supporting information
p. 12910 - 12914
(2014/01/06)
-
- Palladium-catalyzed direct denitrogenative C-3-arylation of 1H-indoles with arylhydrazines using air as the oxidant
-
A novel palladium-catalyzed approach to direct C-3-arylation of 1H-indoles with arylhydrazines using air as the oxidant via C-N bond cleavage has been developed. Various substituents are tolerated in this system in moderate to good yields. This reaction could also be compatible with a larger scale. Thus, this strategy using arylhydrazines as arylating reagents provides a powerful method for constructing substituted 3-aryl-1H-indoles. Copyright
- Chen, Yongxin,Guo, Shuaibo,Li, Kangning,Qu, Jinpeng,Yuan, Hua,Hua, Qiuru,Chen, Baohua
-
supporting information
p. 711 - 715
(2013/03/29)
-
- Copper-catalyzed direct synthesis of 3-arylindoles
-
A direct method for the preparation of various 3-arylindoles from their corresponding nitrosoarenes has been developed. Various substituted nitrosoarenes and alkynes were employed to obtain substituted indoles by using a CuII-Cu0 catalytic system. This is a two-step method that involves annulation of the nitrosoarene and alkyne followed by deoxygenation to give 3-arylindoles. Copyright
- Murru, Siva,Gallo, August A.,Srivastava, Radhey S.
-
experimental part
p. 2035 - 2038
(2011/05/16)
-
- "on water" direct and site-selective Pd-catalysed C-H arylation of (NH)-indoles
-
This communication describes the development of a versatile catalytic system based on palladium(II) acetate/bis(diphenylphosphino)methane [Pd(OAc)2/dppm] that works "on water" giving site-selective C-H arylation of (NH)-indoles without protecting or directing groups. Remarkably, the control of regioselectivity was achieved by small changes in the "extra-catalytic" base/halide partners. These innovative methodologies allow a high-yielding access to both C2 and C3-arylindoles, as well as 2,3-diarylindoles, and display high chemo/regioselectivities and structural versatility with regard to either indole or aryl moieties. Copyright
- Joucla, Lionel,Batail, Nelly,Djakovitch, Laurent
-
supporting information; experimental part
p. 2929 - 2936
(2011/02/22)
-
- Cu(II)-catalyzed direct and site-selective arylation of indoles under mild conditions
-
We have developed a new site-selective Cu(II)-catalyzed C-H bond functionalization process that can selectively arylate indoles at either the C3 or C2 position under mild conditions. The scope of the arylation process is broad and tolerates broad functionality on both the indole and aryl unit, which makes it amenable to further elaboration. The mechanism of the arylation reaction is proposed to proceed via a Cu(III)-aryl species that undergoes initial electrophilic addition at the C3 position of the indole motif. We speculate that site of indole arylation arises through a migration of the Cu(III)-aryl group from C3 to C2, and this can be controlled by the nature of the group on the nitrogen atom; free (NH)- and N-alkylindoles deliver the C3-arylated product, whereas N-acetylindoles afford the C2 isomer, both with excellent yield and selectivity. Copyright
- Phipps, Robert J.,Grimster, Neil P.,Gaunt, Matthew J.
-
supporting information; experimental part
p. 8172 - 8174
(2009/02/02)
-
- Regioselective synthesis of indoles via reductive annulation of nitrosoaromatics with alkynes
-
(equation presented) Indoles are produced regioselectively and in moderate yields by two new processes: (a) from the [Cp*Ru(CO)2]2-catalyzed reaction of nitrosoaromatics (ArNO) with alkynes under carbon monoxide and (b) in a two-step sequence involving the (uncatalyzed) reaction of ArNO with alkynes, followed by reduction of the intermediate adduct.
- Penoni, Andrea,Volkmann, Jerome,Nicholas, Kenneth M.
-
p. 699 - 701
(2007/10/03)
-
- O-heteroaryl, O-alkylheteroaryl, O-alkenylheteroaryl and O-alkynlheteroarylrapamycin derivatives
-
O-Heteroaryl, O-alkylheteroaryl, O-alkenylheteroaryl and O-alkynylheteroarylrapamycin derivatives of the general structural Formula I: STR1 have been prepared from suitable precursors by alkylation and/or arylation at C-42 and/or C-31. These compounds are useful in a mammalian host for the treatment of autoimmune diseases and diseases of inflammation, infectious diseases, the prevention of rejection of foreign organ transplants and the treatment of solid tumors.
- -
-
-
- O-heteroaryl, O-alkylheteroaryl, O-alkenylheteroaryl and O-alkynylheteroarylmacrolides having immunosuppressive activity
-
O-Heteroaryl, O-alkylheteroaryl, O-alkenylheteroaryl and O-alkynylheteroaryl-macrolides of the general structural Formula I: STR1 have been prepared from suitable precursors by alkylation and/or arylation at C-3"" and/or C-4"" of the cyclohexyl ring. These macrolide immunosuppressants are useful in a mammalian host for the treatment of autoimmune diseases, infectious diseases, the prevention of rejection of foreign organ transplants and/or related afflictions, diseases and illnesses.
- -
-
-
- D-heteroaryl, O-alkylheteroaryl, O-alkenylheteroaryl and O-alkynylheteroarylmacrolides having immunosuppressive activity
-
O-Heteroaryl, O-alkylheteroaryl, O-alkenylheteroaryl and O-alkynylheteroarylmacrolides of the general structural Formula I: STR1 have been prepared from suitable precursors by alkylation and/or arylation at C-3" and/or C-4" of the cyclohexyl ring. These macrolide immunosuppressants are useful in a mammalian host for the treatment of autoimmune diseases, infectious diseases, the prevention of rejection of foreign organ transplants and/or related afflictions, diseases and illnesses.
- -
-
-