138409-80-0Relevant academic research and scientific papers
Efficient synthesis of 2,4-disubstituted quinolines: Calix[n]arene- catalyzed Povarov-hydrogen-transfer reaction cascade
Simoes, Juliana Baptista,De Fatima, Angelo,Sabino, Adao Aparecido,Almeida Barbosa, Luiz Claudio,Fernandes, Sergio Antonio
, p. 18612 - 18615 (2014/05/20)
A cascade process involving the Povarov reaction and hydrogen transfer catalyzed with p-sulfonic acid calix[4]arene was disclosed and afforded the synthesis of 2,4-disubstituted quinolines in good yields under appropriate conditions in a single pot proces
Rare-earth metal chlorides catalyzed one-pot syntheses of quinolines under solvent-free microwave irradiation conditions
Zhang, Lijun,Wu, Bing,Zhou, Yongqing,Xia, Jing,Zhou, Shuangliu,Wang, Shaowu
, p. 465 - 471 (2013/08/25)
Under microwave irradiation and solvent-free conditions, rare-earth metal chlorides (RECl3) have been efficient catalysts for one-pot synthesis of quinoline derivatives to give products in good to excellent yields through the multi-component reactions of aldehydes, amines, and alkynes. The rare-earth metal chlorides can be recycled for six times without notable loss of catalytic activities. This new synthetic approach has prominent features of a short reaction time, high yields of products, operational simplicity, broad substrate scopes, environmentally friendly property and commercially available catalysts. It extends the applications of rare-earth metal compounds as catalysts in organic synthesis. A convenient method for the syntheses of quinoline derivatives through multi-component reactions of aldehydes, amines, and alkynes in the presence of rare-earth metal chlorides as catalysts under microwave irradiation and solvent-free conditions was developed.
DDQ-mediated formation of carbon-carbon bonds: Oxidation of imines
Bortolotti,Leardini,Nanni,Zanardi
, p. 10157 - 10174 (2007/10/02)
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.
Annulation Reactions with Iron(III) Chloride: Oxidation of Imines
Leardini, Rino,Nanni, Daniele,Tundo, Antonio,Zanardi, Giuseppe,Ruggieri, Fabrizio
, p. 1842 - 1848 (2007/10/02)
Aromatic imines react with phenylacetylene or styrene in an acetonitrile solution of iron(III) chloride to give quinolines 3 or their tetrahydro derivatives 11 together with variable amounts of products 4 arising from the reduction of the imines.The initial step appears to be a one-electron oxidation to generate iron(II) and an imine radical cation.When the reactions are carried out in the presence of stoichiometric amounts of tetrachloro-p-benzoquinone (chloranil), only quinolines 3 are obtained.
