1027340-20-0Relevant academic research and scientific papers
InBr3-promoted divergent approach to polysubstituted indoles and quinolines from 2-ethynylanilines: Switch from an intramolecular cyclization to an intermolecular dimerization by a type of terminal substituent group
Sakai, Norio,Annaka, Kimiyoshi,Fujita, Akiko,Sato, Asuka,Konakahara, Takeo
, p. 4160 - 4165 (2008)
(Chemical Equation Presented) Use of a 2-ethynylaniline having an alkyl or aryl group on the terminal alkyne selectively produced a variety of polyfunctionalized indole derivatives in moderate to excellent yields via indium-catalyzed intramolecular cyclization of the corresponding alkynylaniline. In contrast, employment of a substrate with a trimethylsilyl group or with no substituent group on the terminal triple bond, exclusively afforded polysubstituted quinoline derivatives in good yields via indium-promoted intermolecular dimerization of the ethynylaniline. This indium catalytic system successfully accommodated the intramolecular cyclization of other arylalkyne skeletons involving a carboxylic acid and an amide group.
Facile Synthesis of π-Conjugated Quinazoline-Substituted Ethenes from 2-Ethynylanilines and Benzonitriles under Transition-Metal-Free Conditions
Wang, Xu,Li, Jiawei,Huang, Yubing,Zhu, Jiayi,Hu, Rongrong,Wu, Wanqing,Jiang, Huanfeng
, p. 10453 - 10464 (2018)
A new transition-metal-free version for the synthesis of π-conjugated quinazoline-substituted ethene derivatives from readily available starting materials has been developed. Quinazoline-substituted ethenes were obtained in moderate to high yields with completely Z-selectivity, and the resulting quinazoline-substituted ethenes show typical aggregation-induced emission (AIE) properties.
Gold-Catalyzed Cascade and Divergent Synthesis of Indolobenzazepines and Indoloquinolines from Nitrogen-Tethered 1,8-Diynes
Ito, Mamoru,Onoda, Hideaki,Shibata, Takanori,Takaki, Asahi
supporting information, (2022/01/22)
We describe the divergent construction of two nitrogen-containing polycyclic systems by gold-catalyzed cycloisomerizations. The gold-catalyzed cascade hydroamination and 7-endo-dig-selective cycloisomerization of nitrogen-tethered 1,8-diynes yielded indol
Palladium-Catalyzed Ligand-Free Double Cyclization Reactions for the Synthesis of 3-(1′-Indolyl)-phthalides
Yuan, Shuo,Zhang, Dan-Qing,Zhang, Jing-Ya,Yu, Bin,Liu, Hong-Min
supporting information, p. 814 - 817 (2020/02/04)
Indole and phthalide are privileged heterocyclic scaffolds in numerous natural products and bioactive molecules. The synthesis and biological evaluation of the compounds combining these two scaffolds have rarely been reported. Herein, we repot the first palladium-catalyzed ligand-free double cyclization reactions that enable efficient synthesis of 3-(1′-indolyl)-phthalides (42 examples, up to 96% yield) under mild conditions. Notably, only 1.0 mol % of catalyst loading is used, suggesting high efficiency. Late-stage elaborations give highly functionalized analogues.
On water: iodine-mediated direct construction of 1,3-benzothiazines from ortho-alkynylanilines by regioselective 6-exo-dig cyclization
Saini, Kapil Mohan,Saunthwal, Rakesh K.,Kumar, Shiv,Verma, Akhilesh K.
supporting information, p. 2657 - 2662 (2019/03/12)
Herein, we report the 6-exo-dig ring closure of ortho-alkynylanilines with readily available aroyl isothiocyanate. An environmentally benign, metal- and base-free, iodine promoted cascade synthesis of highly functionalized (benzo[1,3]thiazin-2-yl)benzimid
[Cp?IrCl2]2-catalysed cyclization of 2-alkynylanilines into indoles
Kumaran, Elumalai,Leong, Weng Kee
supporting information, p. 5495 - 5498 (2014/12/11)
[Cp?IrCl2]2 catalyses the cyclization of 2-alkynylanilines into indoles. A wide variety of substrates is tolerated. A reaction pathway involving intramolecular hydroamination is proposed.
