452070-10-9Relevant academic research and scientific papers
An efficient catalytic method for the Friedl?nder annulation mediated by peptide coupling agent propylphosphonic anhydride (T3P)
Augustine, John Kallikat,Bombrun, Agnes,Venkatachaliah, Srinivasa
experimental part, p. 6814 - 6818 (2012/01/03)
We have demonstrated the utilization of T3P, a mild and low toxic peptide coupling agent, as a promoter and water scavenger in the Friedl?nder annulation, and thus introduced a highly efficient catalytic process to access carbocyclic and heterocyclic fused quinolines under microwave irradiation or a conventional heating technique. The reaction conditions are sufficiently mild to tolerate the acid and base sensitive functional groups that can serve as levers for further extension of the quinoline products.
p-Toluenesulfonic acid promoted annulation of 2-alkynylanilines with activated ketones: Efficient synthesis of 4-Alkyl-2, 3-disubstituted quinolines
Peng, Changlan,Wang, Yong,Liu, Lanying,Wang, Honggen,Zhao, Jiaji,Zhu, Qiang
supporting information; experimental part, p. 818 - 822 (2010/04/02)
Reactions between readily available 2-alkynylanilines and activated ketones such as ss-keto esters promoted by p-toluenesulfonic acid afford 4-alkyl-2, 3-disubstituted quinolines in good to excellent yields. The generality of substituents at the other end of the triple bond of 2-alkynylanilines makes the method a valuable approach to diversified 4-alkylquinolines, which are difficult to obtain by classical methods such as the Friedlaender reaction. Quinoline dimers can be prepared efficiently with alkyl or aryl linkers at C-4.
Chlorotrimethylsilane-mediated friedlaender synthesis of polysubstituted quinolines
Ryabukhin, Sergey V.,Volochnyuk, Dmitriy M.,Plaskon, Andrey S.,Naumchik, Vasiliy S.,Tolmachev, Andrei A.
, p. 1214 - 1224 (2008/02/02)
New convenient conditions for the Friedlander synthesis of quinolines are described. Polysubstituted quinolines were readily prepared using chlorotrimethylsilane as a promoter and water-acceptor agent. Georg Thieme Verlag Stuttgart.
