title: Silver-catalyzed oxidative coupling of aniline and ene carbonyl/acetylenic carbonyl compounds: an efficient route for the synthesis of quinolines.
abstract: An efficient silver-mediated coupling of aniline with ene carbonyl/acetylenic carbonyl compounds for the synthesis of quinolines is reported. The transformation is effective for a broad range of substrates, thus enabling the expansion of substituent architectures on the heterocyclic framework. The electronic properties of the substituents on the amine have been investigated. It was found that molecules with both electron-donating and electron-withdrawing substituents were suitable substrates for this transformation, and the expected products were obtained in moderate to excellent yields. The use of a single catalytic system to mediate chemical transformations in a synthetic operation is important for the development of new atom-economic strategies and this strategy is efficient in building complex structures from simple starting materials in an environmentally benign fashion.
authors.affiliation: School of Chemistry and Pharmacony Engineering, Nanyang Normal University, Wolong Wolong District, Nanyang City, Henan Province Road No. 1638, Fax: (+86) 037763513540. zhangxuedu@126.com.
authors.forename: Xu
authors.initials: X
authors.lastname: Zhang
authors.forename: Xuefeng
authors.initials: X
authors.lastname: Xu
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D000480:Alkynes / Q000737:chemistry*; D000588:Amines / Q000737:chemistry; D000814:Aniline Compounds / Q000737:chemistry*; D002384:Catalysis; D007659:Ketones / Q000737:chemistry; D008698:Mesylates / Q000737:chemistry; D058451:Oxidative Coupling; D011804:Quinolines / Q000138:chemical synthesis / Q000737:chemistry*; D012834:Silver / Q000737:chemistry*
chemical_list: D000447:Aldehydes; D000480:Alkynes; D000588:Amines; D000814:Aniline Compounds; D007659:Ketones; D008698:Mesylates; D011804:Quinolines; D012834:Silver; C012077:trifluoromethanesulfonic acid; C023650:aniline
keywords: acetylenic carbonyl compounds; amines; heterocycles; silver; synthetic methods