Synthesis of Quinolines through Three-Component Cascade Annulation of Aryl Diazonium Salts, Nitriles, and Alkynes

作者: Hao Wang , Qian Xu , Sheng Shen , Shouyun Yu

DOI: 10.1021/ACS.JOC.6B02509

关键词:

摘要: An efficient and rapid synthesis of multiply substituted quinolines is described. This method enabled by a three-component cascade annulation readily available aryl diazonium salts, nitriles, alkynes. reaction catalyst- additive-free. Various alkynes can participate in this transformation, the yields are up to 83%.

参考文章(57)
Brian W. Michel, Laura D. Steffens, Matthew S. Sigman, On the mechanism of the palladium-catalyzed tert-butylhydroperoxide- mediated wacker-type oxidation of alkenes using quinoline-2-oxazoline ligands Journal of the American Chemical Society. ,vol. 133, pp. 8317- 8325 ,(2011) , 10.1021/JA2017043
Simeon Andrews, Steven J. Burgess, Deborah Skaalrud, Jane Xu Kelly, David H. Peyton, Reversal Agent and Linker Variants of Reversed Chloroquines: Activities against Plasmodium falciparum Journal of Medicinal Chemistry. ,vol. 53, pp. 916- 919 ,(2010) , 10.1021/JM900972U
Guillaume Delapierre, Jean Michel Brunel, Thierry Constantieux, Gérard Buono, Design of a new class of chiral quinoline–phosphine ligands. Synthesis and application in asymmetric catalysis Tetrahedron-asymmetry. ,vol. 12, pp. 1345- 1352 ,(2001) , 10.1016/S0957-4166(01)00220-8
Kazuyuki Takahashi, Keiryo Mitsuhashi, Conversion of the carboxyl group to the corresponding trichloromethyl group in the quinoline series Journal of Heterocyclic Chemistry. ,vol. 14, pp. 881- 884 ,(1977) , 10.1002/JHET.5570140531
Nicolas Oger, Erwan Le Grognec, François-Xavier Felpin, Handling diazonium salts in flow for organic and material chemistry Organic chemistry frontiers. ,vol. 2, pp. 590- 614 ,(2015) , 10.1039/C5QO00037H
Margaret M. Biddle, Michael Lin, Karl A. Scheidt, Catalytic enantioselective synthesis of flavanones and chromanes Journal of the American Chemical Society. ,vol. 129, pp. 3830- 3831 ,(2009) , 10.1021/JA070394V
Durga Prasad Hari, Burkhard König, The Photocatalyzed Meerwein Arylation: Classic Reaction of Aryl Diazonium Salts in a New Light Angewandte Chemie. ,vol. 52, pp. 4734- 4743 ,(2013) , 10.1002/ANIE.201210276
Zhonghua Xia, Qiang Zhu, A transition-metal-free synthesis of arylcarboxyamides from aryl diazonium salts and isocyanides. Organic Letters. ,vol. 15, pp. 4110- 4113 ,(2013) , 10.1021/OL4017244