165280-21-7Relevant articles and documents
Metal-Free and syn-Selective Hydrohalogenation of Alkynes through a Pseudo-Intramolecular Process
Asahara, Haruyasu,Mukaijo, Yusuke,Muragishi, Kengo,Iwai, Kento,Ito, Akitaka,Nishiwaki, Nagatoshi
, p. 5747 - 5755 (2021/10/20)
A new metal-free hydrohalogenation method for alkynes has been developed, which proceeds through a pseudo-intramolecular process. In this reaction, ethynylaniline serves as a substrate to quantitatively form an anilinium salt upon treatment with hydrochloric acid. The spatial proximity facilitates the efficient electrophilic addition of HCl to the ethynyl group in syn-mode, affording the corresponding chloroalkene without overaddition. This protocol was applied to HBr and HI, and the corresponding bromo- and iodoalkenes were obtained, respectively. The obtained chloroalkene was converted to tri-substituted alkenes possessing different aryl/alkynyl groups through Pd-catalyzed cross-coupling reactions.
Copper-Catalyzed Aerobic Oxidative Cyclization of 2-Alkynylanilines with Nitrosoarenes: Synthesis of Organic Solid Mechanoluminescence Compounds of 4-Oxo-4 H-cinnolin-2-ium-1-ide
Fang, Xiaolan,Cao, Ji,Ding, Weijie,Jin, Huile,Yu, Xiaochun,Wang, Shun
supporting information, p. 1228 - 1233 (2021/02/20)
An efficient Cu(I)/DMAP/air system for the one-pot synthesis of 4-oxo-4H-cinnolin-2-ium-1-ides, which are often difficult to prepare by traditional routes from substituted 2-alkynylanilines and nitrosoarenes, was developed. These 4-oxo-4H-cinnolin-2-ium-1-ides have practical applications as mechanoluminescent materials. Preliminary mechanistic experiments were performed, and a plausible mechanism for this tandem process is proposed. The use of an inexpensive copper catalyst and molecular oxygen as the oxygen source and the oxidant make this an attractive green protocol with potential synthetic applications.
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.
Intramolecular activation of imidate with cationic gold(I) catalyst: A new benzylation reaction of alcohols
Ban, Shintaro,Endo, Tomotake,Matsui, Rikako,Morita, Nobuyoshi,Hashimoto, Yoshimitsu,Tanaka, Kosaku,Tamura, Osamu
, (2020/08/28)
Benzylation of alcohols with benzyl (Z)-2,2,2-trifluoro-N-(2-alkynylphenyl)acetimidates 5a-f in the presence of a cationic gold(I) catalyst was investigated. Reagent 5f was the most effective, affording benzyl ethers in good yields. Our results indicate that these gold(I)-activated imidates are effective leaving groups.
Compositions for Treatment of Cystic Fibrosis and Other Chronic Diseases
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Paragraph 1669, (2015/09/22)
The present invention relates to pharmaceutical compositions comprising an inhibitor of epithelial sodium channel activity in combination with at least one ABC Transporter modulator compound of Formula A, Formula B, Formula C, or Formula D. The invention also relates to pharmaceutical formulations thereof, and to methods of using such compositions in the treatment of CFTR mediated diseases, particularly cystic fibrosis using the pharmaceutical combination compositions.
[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.
COMPOSITIONS FOR TREATMENT OF CYSTIC FIBROSIS AND OTHER CHRONIC DISEASES
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, (2012/04/23)
The present invention relates to pharmaceutical compositions comprising an inhibitor of epithelial sodium channel activity in combination with at least one ABC Transporter modulator compound of Formula A, Formula B, Formula C, or Formula D. The invention also relates to pharmaceutical formulations thereof, and to methods of using such compositions in the treatment of CFTR mediated diseases, particularly cystic fibrosis using the pharmaceutical combination compositions.
Domino process in silver-catalyzed reactions of N-arylformimidates and active methylene compounds involving cycloisomerization and 1,3-alkenyl shift
Oh, Chang Ho,Karmakar, Swastik,Park, HyoSeung,Ahn, YoungCheon,Kim, Jung Wook
supporting information; experimental part, p. 1792 - 1793 (2010/04/23)
(Formula Presented) We have developed an efficient method for the synthesis of 2,3-disubstituted indoles from alkyne iminoethers 1 that employs a domino process involving Ag-catalyzed condensation followed by a tandem Ag-induced cycloisomerization and 1,3
One-pot/four-step/palladium-catalyzed synthesis of indole derivatives: The combination of heterogeneous and homogeneous systems
Sakai, Hayato,Tsutsumi, Ken,Morimoto, Tsumoru,Kakiuchia, Kiyomi
supporting information; experimental part, p. 2498 - 2502 (2009/08/14)
One-pot, four-step syntheses of indoles using both solid-supported heterogeneous and homogeneous palladium catalysts and reagents were carried out. Such a combination of these two-phase catalysts and reagents causes a dramatic increase in yield, and it is a simple process. The presented methodology is effective for four-step reactions to provide various functionalized indoles.
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 (2008/09/21)
(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.
