73013-72-6

Upstream product

• 4187-87-5 1-Phenyl-2-propyn-1-ol 
• 33348-34-4 4-amino-3-iodobenzonitrile 
• 104-54-1 3-Phenylpropenol 
• 873-74-5 4-Aminobenzonitrile 
• 300-57-2 allylbenzene 
• 102904-41-6 (E)-4-((phenylimino)methyl)benzonitrile 
• 108-05-4 vinyl acetate 

Relevant academic research and scientific papers

Palladium-catalyzed synthesis of quinolines from allyl alcohols and anilines

A process for quinoline synthesis through palladium-catalyzed oxidative cyclization of aryl allyl alcohols and anilines is described. This process works in the absence of acid, base and any other additive and has a broad substrate scope, tolerating electron-withdrawing groups such as nitryl, trifluoromethyl and so on. A series of quinolines are prepared in satisfactory yields.

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.

Rapid one-pot synthesis of antiparasitic quinolines based upon the microwave-assisted coupling-isomerization reaction (MACIR)

2-Substituted quinolines and related derivatives can be rapidly prepared from (hetero)aryl halides and propargyl alcohols in the sense of a one-pot microwave-assisted coupling-isomerization reaction (MACIR). First biological tests against trypanosomes and protozoans have revealed antiparasitic activity in the lower micromolar range. Georg Thieme Verlag Stuttgart.

DDQ-mediated formation of carbon-carbon bonds: Oxidation of imines

The reaction of imines with alkynes and alkenes, in the presence of 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ), to give quinoline derivatives is described. The mechanism of the annulation is discussed, and evidence supporting a non-concerted pathway, at least when the alkene is butyl vinyl ether, is reported. Preliminary information is also given about solid adducts of imines with DDQ, which do not seem to be involved in the reaction path leading to quinolines, and should account for the dependence of product yields on the position of substituents on the starting imines.