108378-76-3Relevant academic research and scientific papers
Chiral Br?nsted Acid from Chiral Phosphoric Acid Boron Complex and Water: Asymmetric Reduction of Indoles
Yang, Kai,Lou, Yixian,Wang, Chenglan,Qi, Liang-Wen,Fang, Tongchang,Zhang, Feng,Xu, Hetao,Zhou, Lu,Li, Wangyang,Zhang, Guan,Yu, Peiyuan,Song, Qiuling
, p. 3294 - 3299 (2020/01/21)
A new chiral Br?nsted acid, generated in situ from a chiral phosphoric acid boron (CPAB) complex and water, was successfully applied to asymmetric indole reduction. This “designer acid catalyst”, which is more acidic than TsOH as suggested by DFT calculations, allows the unprecedented direct asymmetric reduction of C2-aryl-substituted N-unprotected indoles and features good to excellent enantioselectivities with broad functional group tolerance. DFT calculations and mechanistic experiments indicates that this reaction undergoes C3-protonation and hydride-transfer processes. Besides, bulky C2-alkyl-substituted N-unprotected indoles are also suitable for this system.
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.
The Development of a Palladium-Catalyzed Tandem Addition/Cyclization for the Construction of Indole Skeletons
Yu, Shuling,Qi, Linjun,Hu, Kun,Gong, Julin,Cheng, Tianxing,Wang, Qingzong,Chen, Jiuxi,Wu, Huayue
, p. 3631 - 3638 (2017/04/11)
A palladium-catalyzed tandem addition/cyclization of 2-(2-aminoaryl)acetonitriles with arylboronic acids has been developed for the first time, achieving a new strategy for direct construction of indole skeletons. This system shows good functional group tolerance and remarkable chemoselectivity. In particular, the halogen (e.g., bromo and iodo) substituents are amenable to further synthetic elaborations thereby broadening the diversity of the products. Preliminary mechanistic experiments indicate that this transformation involves sequential nucleophilic addition followed by an intramolecular cyclization.
Access to 2-Arylindoles via Decarboxylative C?C Coupling in Aqueous Medium and to Heteroaryl Carboxylates under Base-Free Conditions using Diaryliodonium Salts
Arun, Velladurai,Pilania, Meenakshi,Kumar, Dalip
supporting information, p. 3345 - 3349 (2016/12/14)
Easily accessible heteroaromatic carboxylic acids and diaryliodonium salts were successfully employed to construct valuable 2-arylindoles and heteroaryl carboxylates in a regioselective fashion. C2-arylated indoles were produced using a Pd-catalyzed decarboxylative strategy in water without any base, oxidant, or ligand. Heteroaryl carboxylates were prepared under metal and base-free conditions. This protocol was successfully utilized to synthesize Paullone, a cyclin-dependent kinase (CDK) inhibitor.
Microwave irradiated synthesis of 2-bromo(chloro)indoles via intramolecular cyclization of 2-(gem-dibromo(chloro)vinyl)anilines in the presence of TBAF under metal-free conditions
Wang, Min,Li, Pinhua,Chen, Wei,Wang, Lei
, p. 26918 - 26923 (2014/07/21)
2-Bromo(chloro)indoles were readily and efficiently prepared through TBAF-promoted intramolecular cyclization of 2-(gem-dibromo(chloro)vinyl)anilines in excellent yields under metal-free and microwave irradiation conditions. This journal is the Partner Organisations 2014.
The facile synthesis of 2-bromoindoles via Cs2CO 3-promoted intramolecular cyclization of 2-(gem-dibromovinyl)anilines under transition-metal-free conditions
Li, Pinhua,Ji, Yong,Chen, Wei,Zhang, Xiuli,Wang, Lei
, p. 73 - 78 (2013/03/29)
2-Bromoindoles were readily prepared through a facile Cs2CO 3-promoted intramolecular cyclization of 2-(gem-bromovinyl)-N- methylsulfonylanilines in excellent yields under transition-metal-free conditions. This methodology could be extended to the synthesis of corresponding 2-chloroindoles. The reaction mechanism suggested that cyclization occurs through a key intermediate, phenylethynyl bromide, followed by cyclization in one-pot. The Royal Society of Chemistry.
Some new derivatives of 5-aryl-,2,5-diaryland 2-ethoxycarbonyl-5-aryl- indoles
Chikvaidze, Ioseb Sh.,Barbakadze, Nana N.,Samsoniya, Shota A.
experimental part, p. 143 - 154 (2012/05/05)
Some derivatives of 5-aryl-, 2.5-diaryl-, and 2-ethoxycarbonyl-5-aryl- indoles are synthesized. Some reactions of ethyl 5-phenylindole-2-carboxylate are described. It is revealed that an α-ethoxycarbonyl group has a steric and electron-acceptor influence on indole substitution reactions. The structures of all novel compounds are confirmed by IR, UV, 1H NMR, 13C NMR and elemental analyses. ARKAT-USA, Inc.
SYNTHESIS OF 2-ARYLINDOLES via CONDENSATION OF ortho-AMINOBENZYL SULFONES WITH AROMATIC ALDEHYDES
Wojciechowski, Krzysztof,Makosa, Mieczyslaw
, p. 671 - 674 (2007/10/02)
ortho-Aminobenzyl sulfones condensed with aromatic aldehydes to give Schiff bases, wich in strong alkaline medium undergo transformations into 2-arylindoles.
