49634-76-6

Upstream product

• 100-58-3 phenylmagnesium bromide 
• 108-86-1 bromobenzene 
• 25428-06-2 2-amino-5-methyl-acetophenone 
• 98-80-6 phenylboronic acid 
• 5925-93-9 2-amino-5-methylbenzonitrile 
• 106-49-0 p-toluidine 
• 536-74-3 phenylacetylene 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 17852-28-7 2-amino-5-methylbenzophenone 

Downstream Products

• 1346154-99-1 N-allyl-N-benzyl-4-methyl-2-(α-phenylstyryl)aniline 
• 1346155-04-1 N-benzyl-6-methyl-4-phenyl-2-quinolone 
• 73402-92-3 2,4-diphenyl-6-methylquinoline 
• 394240-16-5 2-(4-methylphenyl)-4-phenyl-6-methylquinoline 
• 71858-10-1 2-(4-methoxyphenyl)-4-phenyl-6-methylquinoline 
• 56366-15-5 5-methyl-3-phenyl-1H-indole 
• 70453-82-6 6-methyl-4-phenyl-1,2-dihydroquinolin-2-one 
• 76061-97-7 4-Phenyl-6-methylquinoline 

Relevant academic research and scientific papers

Bischler-Napieralski Synthesis of 6-Alkynyl Phenanthridines Based on Tf2O-Promoted Electrophilic Activation of N-Aryl-2-propynamides

An efficient method for the synthesis of 6-alkynyl phenanthridines was developed. The method offered the first example to use 2-propynamides as substrates in the Bischler-Napieralski reaction and to create alkynylnitrilium triflates as new active intermediates in organic synthesis.

PEG-400 as a carbon synthon: Highly selective synthesis of quinolines and methylquinolines under metal-free conditions

A metal-free, peroxide-free, and efficient procedure for the highly selective synthesis of quinolines and methylquinolines was reported. The main feature of this method was that the same substrate can produce quinolines and methylquinolines, respectively, under different reaction conditions. PEG-400 was used as both a reactant and solvent in this reaction. The utility of the designed procedure was also demonstrated by the derivatization of the products to bioactive compounds. This journal is

Photocatalyzed Intramolecular [2+2] Cycloaddition of N-Alkyl-N-(2-(1-arylvinyl)aryl)cinnamamides

N-Alkyl-N-(2-(1-arylvinyl)aryl)cinnamamides are converted into natural product inspired scaffolds via iridium photocatalyzed intramolecular [2+2] photocycloaddition. The protocol has a broad substrate scope, whilst operating under mild reaction conditions. Tethering four components forming a trisubstituted cyclobutane core builds rapidly high molecular complexity. Our approach allows the design and synthesis of a variety of tetrahydrocyclobuta[c]quinolin-3(1H)-ones, in yields ranging between 20–99 %, and with excellent regio- and diastereoselectivity. Moreover, it was demonstrated that the intramolecular [2+2]-cycloaddition of 1,7-enynes—after fragmentation of the cyclobutane ring—leads to enyne-metathesis-like products.

Mn(III)-Mediated Regioselective 6-endo-trig Radical Cyclization of o-Vinylaryl Isocyanides to Access 2-Functionalized Quinolines

A Mn(III)-mediated radical cyclization reaction of o-vinylaryl isocyanides and arylboronic acids or diphenylphosphine oxides to access various 2-functionalized quinolines under mild conditions was developed. With the introduction of radical stabilizing substituents (e. g. aryl and methyl group) on vinyl group, this reaction provides a regiospecific 6-endo-trig radical cyclization of o-vinylaryl isocyanides, giving a number of structurally unique and biologically potential 2-functionalized quinoline derivatives.

Iodine-Promoted Synthesis of 4-Aryl-2-(arylsulfonyl)quinolones by Desulfurative C-S Cross-Coupling Reaction of Quinoline-2-thiones with Sodium Sulfinates

An iodine-induced sulfonylation of quinoline-2-thiones with sodium arenesulfinates as sulfur sources for the synthesis of 4-aryl-2-(arylsulfonyl)quinoline derivatives is described. The 4-aryl-2-(arylsulfonyl)quinoline derivatives can be obtained in a moderate to good yields. This C-S bond cleavage and C-S cross-coupling proceeds in the absence of a metal under inexpensive and nontoxic conditions and it displays a broad substrate scope.

Palladium-Catalyzed/Copper-Mediated Desulfurization and Aryl- ation of Quinoline-2-(1 H)-thione for Rapid Access to Quinoline Derivatives

An efficient method for carbon-carbon bond formation is described. The process employs the palladium-catalyzed and copper-mediated cross-coupling of quinoline-2-(1 H)-thiones with arylboronic acids or alkynes through C-S bond cleavage without an inert atm

A heterogeneous catalytic and solvent-free approach to 1,2-dihydroquinoline derivatives from aromatic amines and alkynes by tandem hydroarylation-hydroamination

This study describes a mesoporous aluminosilicate (ASM) catalyst-induced one-step synthesis of substituted dihydroquinolines through a hydroarylation/hydroamination cascade reaction under solvent-free conditions. A sol-gel method was utilized to prepare t

Enantioselective Copper-Catalyzed Borylative Cyclization with Cyclic Imides

An enantioselective borylative cyclization cascade utilizing cyclic imides has been developed. We employ a highly enantioselective borylcupration process that includes a 1,2-addition to a cyclic imide. The products contain a valuable hemiaminal and boronate handle for further elaborations within a congested framework. This work demonstrates the utility of cyclic imides as simple precursors to unlock access to sought-after polycyclic indolines. Futhermore, this report highlights the capability to harness reactive catalytic intermediates to exploit otherwise unreactive functional groups.

Iron-Promoted Construction of Indoles via Intramolecular Oxidative C-N Coupling of 2-Alkenylanilines Using Persulfate

Indole scaffold synthesis relies primarily on oxidative C-H amination of N-protected alkenylanilines for C-N intramolecular cyclization reactions. Herein, for the first time, without N-protection, various readily prepared 2-alkenylanilines were transformed into the desired indole products in good yields by using K 2 S 2 O 8 as oxidant in the presence of catalytic amounts of FeF 2. The K 2 S 2 O 8 /FeF 2 system offers a direct and benign synthetic route to 3-arylindoles and it is applicable to a wide range of substituted indoles including drug intermediates.

Chemo- And Regioselective Magnesium-Catalyzed ortho-Alkenylation of Anilines

A simple and efficient catalytic system for a chemo- and regioselective ortho-alkenylation of anilines is presented. The new magnesium-catalyzed reaction allows the use of a wide range of alkynes and anilines with different electronic and steric propertie