606146-17-2

Upstream product

• 10147-11-2 propargyl benzene 
• 615-43-0 2-iodophenylamine 
• 615-36-1 2-bromoaniline 

Downstream Products

• 1234333-46-0 (+)-(R)-2-benzylindoline 
• 76691-97-9 2-(3-phenylpropyl)aniline 
• 24005-23-0 2-phenyl-1,2,3,4-tetrahydroquinoline 
• 164398-38-3 2-(3-Phenylpropyl)phenyl azide 
• 1632138-06-7 C₂₃H₂₃NO₄ 
• 1632137-92-8 C₃₀H₂₉NO₆S 
• 1201632-39-4 C₁₆H₁₄N₂O 
• 1220451-76-2 C₂₁H₂₁NO₂ 
• 870987-41-0 1-benzyl-3,4-bis-(2-benzyl-1H-indol-3-yl)-pyrrole-2,5-dione 
• 3377-72-8 2-benzylindole 

Relevant academic research and scientific papers

Palladium-Catalyzed Ligand-Free Double Cyclization Reactions for the Synthesis of 3-(1′-Indolyl)-phthalides

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.

A Synthetic Route to Chiral Benzo-Fused N-Heterocycles via Sequential Intramolecular Hydroamination and Asymmetric Hydrogenation of Anilino-Alkynes

An efficient sequential intramolecular hydroamination/asymmetric hydrogenation reaction under catalysis of a single chiral ruthenium complex or a binary system consisting of achiral gold complex and chiral ruthenium complex has been reported. A diverse range of enantioenriched benzo-fused N-heterocycles, including 1,2,3,4-tetrahydroquinoline, indoline, and 2,3,4,5-tetrahydro-1H-benzo[b]azepine derivatives, were obtained from anilino-alkynes in high yields (up to 98%) with moderate to excellent enantioselectivities (up to 98% ee) under mild conditions. This protocol features good functional group tolerance and high atom economy. Furthermore, this catalytic protocol is applicable to gram-scale synthesis of a naturally occurring alkaloid, (-)-Angustureine.

One-Pot Synthesis of N-Imidoyl-(1 H)-indoles via Palladium-Catalyzed Oxidative Insertion Domino Reaction with Isocyanide and Arylboronic Acid

Efficient one-pot synthesis of N-imidoyl-(1H)-indoles has been described, which is achieved by the palladium-catalyzed oxidative insertion of 2-(phenylethynyl)aniline, arylboronic acid, and isonitrile. This method provides a new way to synthesize N-imidoy

Iron-Catalyzed Intramolecular Aminations of C(sp3)?H Bonds in Alkylaryl Azides

The nucleophilic iron complex Bu4N[Fe(CO)3(NO)] (TBA[Fe]) catalyzes the direct intramolecular amination of unactivated C(sp3)?H bonds in alkylaryl azides, which results in the formation of substituted indoline and tetrahydroquinoline derivatives.

Palladium-catalyzed diastereoselective oxyarylation of 2-alkylindoles

Diastereoselective oxyarylation of N-protected 2-alkylindoles with commercially available boronic acids and TEMPO as a mild oxidant to give N-protected 2-aryl-2-alkyl-3-(2-chloroacetoxy)indolines is described. Reactions are easy to conduct, and product indolines containing a fully substituted C-center are obtained in good yields with good to excellent selectivities.

p-Toluenesulfonic acid promoted annulation of 2-alkynylanilines with activated ketones: Efficient synthesis of 4-Alkyl-2, 3-disubstituted quinolines

Reactions between readily available 2-alkynylanilines and activated ketones such as ss-keto esters promoted by p-toluenesulfonic acid afford 4-alkyl-2, 3-disubstituted quinolines in good to excellent yields. The generality of substituents at the other end of the triple bond of 2-alkynylanilines makes the method a valuable approach to diversified 4-alkylquinolines, which are difficult to obtain by classical methods such as the Friedlaender reaction. Quinoline dimers can be prepared efficiently with alkyl or aryl linkers at C-4.

Thiocarbonyl induced heterocumulenic Pauson-Khand type reaction: Expedient synthetic method for thieno[2,3-b]indol-2-ones

The first examples of C=S induced Pauson-Khand type reactions are described; 2-alkynylphenyl isothiocyanates were converted to 3-substituted-2H-thieno[2,3-b]indol-2-ones in the presence of a stoichiometric amount of Mo(CO)6 or Co2(CO

Configurational stability of bisindolylmaleimide cyclophanes: From conformers to the first configurationally stable, atropisomeric bisindolylmaleimides

The bisindolylmaleimides are selective protein kinase inhibitors that can adopt two limiting diastereomeric (syn and anti) conformations. The configurational stability of a range of substituted and macrocyclic bisindolylmaleimides was investigated by using appropriate techniques. With unconstrained bisindolylmaleimides, the size of the 2-indolyl substituents was found to affect configurational stability, though not sufficiently to allow atropisomeric bisindolylmaleimides to be obtained. However, with a tether between the two indole nitrogen atoms in place, the steric effect of 2-indolyl substituents was greatly exaggerated, leading to large differences in configurational sta bility. The rate of interconversion of the syn and anti conformers varied by over twenty orders of magnitude through substitution of a bisindolylmaleimide ring system, which was constrained within a macrocyclic ring. Indeed, the first examples of configurationally stable atropisomeric bisindolylmaleimides are reported; the half-life for epimerisation of these compounds at room temperature was estimated to be > 107 years.

Biradicals/zwitterions from enallene-isonitriles. Formal [4 + 1] cycloadditions leading to 11H-indeno[1,2-b]quinoline and related compounds

1,3-Prototropic rearrangement of the benzannulated enyne-isonitriles to the corresponding enallene-isonitriles followed by cycloaromatization generated the putative quinoline biradicals/zwitterions. A subsequent intramolecular radical-radical coupling or electrophilic aromatic substitution then gave the formal [4 + 1] cycloaddition adducts leading to 11H-indeno[1,2-b]quinoline and related compounds.