46870-92-2

Upstream product

• 4173-65-3 3-[(4-methoxyphenyl)amino]-1-phenylpropan-1-one 
• 345928-12-3 6-Methoxy-4-phenyl-quinoline-2-carboxylic acid 
• 34241-39-9 azobisisobutyronitrile 
• 10349-38-9 p-methoxyphenylisonitrile 
• 536-74-3 phenylacetylene 
• 50-00-0 formaldehyd 
• 104-94-9 4-methoxy-aniline 
• 104-55-2 3-phenyl-propenal 
• 2579-22-8 Phenylpropargyl aldehyde 
• 60-12-8 2-phenylethanol 
• 32328-80-6 N-(4-methoxyphenyl)methylenamine 
• 67-68-5 dimethyl sulfoxide 
• 102921-26-6 (1,2-dibromoethyl)benzene 
• 16717-64-9 1-azidostyrene 

Downstream Products

• 76061-96-6 4-Phenyl-6-methoxy-1,2,3,4-tetrahydroquinoline 
• 76061-92-2 1-Chloroacetyl-4-phenyl-6-methoxy-1,2,3,4-tetrahydroquinoline 

Relevant academic research and scientific papers

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

Copper-mediated formal [5+1] annulation of 2-vinylanilines and glyoxylic acid: A facile approach for the synthesis of 4-arylated quinolines

A copper-mediated formal [5 + 1] oxidative annulation of 2-vinylanilines and glyoxylic acid to 4-arylated quinolines was developed. A series of 4-arylated quinoline derivatives were obtained in good to excellent yields. This protocol could be carried out efficiently on gram scale. The transformation probably underwent nucleophilic addition/6π electrocyclization/oxidative aromatization and the elimination of CO2 cascade processes.

DMSO/t-BuONa/O2-Mediated Aerobic Dehydrogenation of Saturated N-Heterocycles

Aromatic N-heterocycles such as quinolines, isoquinolines, and indolines are synthesized via sodium tert-butoxide-promoted oxidative dehydrogenation of the saturated heterocycles in DMSO solution. This reaction proceeds under mild reaction conditions and has a good functional group tolerance. Mechanistic studies suggest a radical pathway involving hydrogen abstraction of dimsyl radicals from the N-H bond or α-C-H of the substrates and subsequent oxidation of the nitrogen or α-aminoalkyl radicals.

Direct Synthesis of Quinolines via Co(III)-Catalyzed and DMSO-Involved C-H Activation/Cyclization of Anilines with Alkynes

A unique Co(III)-catalyzed and DMSO-involved C-H activation/cyclization of simple, cheap, and easily available anilines with alkynes for direct and highly efficient synthesis of privileged quinolines with exclusive regioselectivity and broad substrate/functional group tolerance and in good to excellent yields, where DMSO was employed as both the solvent and the C1 building block of quinoline products, is reported. Mechanistic experiments revealed that the versatile reaction might employ the 2-vinylbenzenamine species as the active intermediate.

Direct Assembly of 4-Substituted Quinolines with Vinyl Azides as a Dual Synthon via C=C and C-N Bond Cleavage

An unprecedented Zn-promoted selective cleavage of vinyl azides for the synthesis of 4-substituted quinolines is developed. In this conversion, vinyl azides function as a dual synthon via C=C and C-N bond cleavage with two C=C bonds and one C=N bond formation in a one-step manner. The reaction is appreciated for its readily accessible substrates, high step economy, mild conditions, and use of air as the sole oxidant.

Synthesis of quinolines from anilines, acetophenones and DMSO under air

An efficient CH3SO3H-promoted synthesis of quinolines from readily available anilines, acetophenones and DMSO under air is reported. This protocol gives diverse substituted 4-arylquinolines in moderate to high yields with broad substrate/functional group tolerance. Preliminary mechanistic studies demonstrate that DMSO may be transformed to HCHO in this process and used as a one carbon source.

Silver-Catalyzed Minisci Reactions Using Selectfluor as a Mild Oxidant

A new method for silver-catalyzed Minisci reactions using Selectfluor as a mild oxidant is reported. Heteroarenes and quinones both participate in radical C-H alkylation and arylation from a variety of carboxylic and boronic acid radical precursors. Several oxidatively sensitive and highly reactive radical species are successful, providing structures that are challenging to access by other means.

Carbon annulation of ortho-vinylanilines with dimethyl sulfoxide to access 4-aryl quinolines

A palladium-catalyzed annulation of ortho-vinylanilines with dimethyl sulfoxide was developed to access 4-aryl quinolines in moderate to good yields. Activated by 1,4-diazabicyclo[2.2.2]octane bis(sulfur dioxide) adduct (DABSO), DMSO served as a “=CH-” fragment in this transformation. It represents a facile pathway leading to 4-aryl quinolines.

Silver-catalyzed three-component approach to quinolines starting from anilines, aldehydes, and alcohols

A silver-catalyzed sequential formation of two C-C bonds for the construction of a series of polysubstituted quinolines from anilines, aldehydes, and alcohols under mild conditions has been developed. The transformation is effective for a broad range of substrates, including aliphatic alcohols, arylalkanols, cycloalkanols, and ethylene glycol, thereby permitting the expansion of the constituent architectures of the heterocyclic framework.

HOTf-catalyzed intermolecular hydroamination reactions of alkenes and alkynes with anilines

Herein, the intermolecular hydroamination of alkenes and alkynes with anilines catalyzed by HOTf under mild conditions has been developed. This reaction provides one of the simplest alkene and alkyne addition methods and is an alternative to metal-catalyzed reactions. At the same time, the intramolecular hydroamination of alkynes with anilines proceeds smoothly to obtain quinolines. We found that this strategy is efficient in building complex structures from simple starting materials in an environmentally benign fashion.