1075185-76-0

Upstream product

• 67-68-5 dimethyl sulfoxide 
• 108-69-0 3,5-dimethylaminoaniline 
• 98-86-2 acetophenone 
• 16169-88-3 1-phenylprop-2-ynyl acetate 
• 300-57-2 allylbenzene 
• 100-52-7 benzaldehyde 

Relevant academic research and scientific papers

Synthesis of quinolines through copper-catalyzed intermolecular cyclization reaction from anilines and terminal acetylene esters

A simple and convenient copper-catalyzed intermolecular cyclization reaction for the synthesis of quinolines from anilines and terminal acetylene esters has been developed. This methodology constructs the C-N and C-C bonds successively via a cascade process, and provides the desired products in moderate to good yields.

Copper-Catalyzed Aerobic Oxidative Cyclization of Anilines, Aryl Methyl Ketones and DMSO: Efficient Assembly of 2-Arylquinolines

A Cu-catalyzed C?H cyclization of simple anilines with ketones and DMSO as a one-carbon source has been developed. Using an aerobic oxidative protocol, a number of ketones and anilines could be easily converted to 2-arylquinolines, rather than 4-arylquinolines, thus providing a highly atom-economical and simple approach to biologically significant 2-arylquinolines. Based on the preliminary experiments, a plausible mechanism is proposed. (Figure presented.).

Method for synthesizing quinoline by oxidizing and cyclizing acetophenone and aniline compound

The invention discloses a method for synthesizing quinoline by oxidizing and cyclizing acetophenone and aniline compound. According to the method, acetophenone, aniline compound and dimethyl sulfoxidegenerate one-pot reaction to obtain quinoline in an oxygen containing atmosphere under existence of a copper salt catalyst. The method enriches quinoline varieties, provides more intermediates for pharmaceutical synthesis and further has the advantages of wide raw material source, simple step, moderate reaction condition, high yield and benefit to industrial production.

Synthesis method of polysubstituted quinoline

The invention discloses a synthesis method of polysubstituted quinolone. The method comprises the step: in an oxygen-containing atmosphere, enabling acetophenone, an aniline compound and dimethyl sulfoxide to react in a pot in the presence of an iron salt and/or ferrous salt catalyst so as to obtain the polysubstituted quinolone. By adopting the method disclosed by the invention, the variety of quinolone derivatives is enriched and more intermediates are provided for medicine synthesis; the synthesis method has the advantages of wide raw material sources, simple steps, moderate reaction conditions and high yield and industrial production is facilitated.

Palladium-Catalyzed Allylic C-H Oxidative Annulation for Assembly of Functionalized 2-Substituted Quinoline Derivatives

An efficient and practical palladium-catalyzed aerobic oxidative approach to afford functionalized 2-substituted quinolines in moderate to good yields from readily available allylbenzenes with aniline is developed. The present annulation process has high functional-group tolerance and high atom economy, making it a valuable and practical method in synthetic and medicinal chemistry. Moreover, this transformation is supposed to proceed through oxidation of allylic C-H functionalization to form C-C and C-N bonds in one pot.

Diastereoselective, multicomponent access to trans-2-aryl-4-arylamino-1,2, 3,4-tetrahydroquinolines via an AA′BC sequential four-component reaction and their application to 2-arylquinoline synthesis

The CAN-catalyzed reaction between 3,5-disubstituted anilines, vinyl ethers and aromatic aldehydes leads to trans-2-aryl-4-arylaminotetrahydroquinolines, in an AA′BC sequential multicomponent transformation related to the Povarov reaction that was also extended to the use of a second aniline as the C-4 substituent. The unusual trans stereochemistry was explained by stabilization of the corresponding intermediate by intramolecular hydrogen bonding. The presence of the 4-anilino substituent allowed adapting the method to the synthesis of 4-unsubstituted 2-arylquinolines, by treatment of the crude product from the MCR with FeCl3 in methanol.

Anti-leishmanial evaluation of C2-aryl quinolines: Mechanistic insight on bioenergetics and sterol biosynthetic pathway of Leishmania braziliensis

A series of diverse simple C2-aryl quinolines was synthesized de novo via a straightforward synthesis based on the acid-catalyzed multicomponent imino Diels-Alder reactions. Seven selected quinolines were evaluated at different stages of Leishmania braziliensis parasite. Among them, the 6-ethyl-2- phenylquinoline 5f was able to inhibit the growth of promastigotes of this parasite without affecting the mammalian cells viability and decreasing the number of intracellular L. braziliensis amastigotes on BMDM macrophages. The mechanism of action studied for the selected compound consisted in: (1) alteration of parasite bioenergetics, by disrupting mitochondrial electrochemical potential and alkalinization of acidocalcisomes, and (2) inhibition of ergosterol biosynthetic pathway in promastigote forms. These results validate the efficiency of quinoline molecules as leishmanicide compounds.

In vitro antifungal activity of polyfunctionalized 2-(hetero)arylquinolines prepared through imino Diels-Alder reactions

Diverse polyfunctionalized quinolines, easily prepared using Lewis acid-catalyzed imino Diels-Alder reactions between corresponding aldimines, were tested for antifungal properties against standardized as well as clinical isolates of clinically important fungi. Among them, 4-pyridyl derivatives displayed the best activities mainly against dermatophytes. The activity appears not to be related neither to the lipophilicity nor to the basicity of compounds.