Microwave-Assisted and Yb(OTf)₃-Promoted One-Pot Multicomponent Synthesis of Substituted Quinolines in Ionic Liquid

Abstract

A straightforward and efficient method has been developed for the synthesis of quinolines by Yb(OTf)₃ catalyzed three-component reaction of aldehydes, alkynes, and amines under microwave irradiation in ionic liquid. A series of 2,4-disubstituted quinolines was synthesized in excellent yield (69-93%) under mild reaction condition and the catalyst was recycled for four cycles.

Key words

microwave assisted - ytterbium triflate - one-pot - multicomponent - quinolines - ionic liquid

References and Notes

• 1 Michael JP. Nat. Prod. Rep.  2008,  25:  166 
• 2a Foley M. Tilley L. Int. J. Parasitol.  1997,  27:  231 
• 2b Egan TJ. Expert Opin. Ther. Pat.  2001,  11:  185 
• 3 McCormick JL. McKee TC. Cardellina JH. Boyd MR. J. Nat. Prod.  1996,  59:  469 
• 4a Eswaran S. Adhikari AV. Chowdhury IH. Pal NK. Thomas KD. Eur. J. Med. Chem.  2010,  3374 
• 4b de Souza MV. Pais KC. Kaiser CR. Peralta MA. de L Ferreira M. Lourenço MC. Bioorg. Med. Chem.  2009,  17:  1474 
• 4c Vangapandu S. Jain M. Jain R. Kaur S. Singh PP. Bioorg. Med. Chem.  2004,  12:  2501 
• 5a Eswaran S. Adhikari AV. Shetty NS. Eur. J. Med. Chem.  2009,  4637 
• 5b Musiol R. Serda M. Hensel-Bielowka S. Polanski J. Curr. Med. Chem.  2010,  17:  1960 
• 5c Musiol R. Jampilek J. Buchta V. Silva L. Niedbala H. Podeszwa B. Palka A. Majerz-Maniecka K. Oleksyn B. Polanski J. Bioorg. Med. Chem.  2006,  15:  3592 
• 6a Heiniger B. Gakhar G. Prasain K. Hua DH. Nguyen TA. Anticancer Res.  2010,  30:  3927 
• 6b Fujimoto S. Biol. Pharm. Bull.  2007,  1923 
• 7a Korivi RP. Cheng C.-H. J. Org. Chem.  2006,  71:  7079 
• 7b Sarma R. Prajapati D. Synlett  2008,  3001 
• 7c Lekhok KC. Prajapati D. Boruah RC. Synlett  2008,  655 
• 7d Zhang Z. Tang J. Wang Z. Org. Lett.  2008,  10:  173 
• 7e Sandelier MJ. DeShong P. Org. Lett.  2007,  9:  3209 
• 8a Dömling A. Ugi I. Angew. Chem. Int. Ed.  2000,  39:  3168 
• 8b Dömling A. Chem. Rev.  2006,  106:  17 
• 8c Sunderhaus JD. Martin SF. Chem. Eur. J.  2009,  15:  1300 
• 8d Ramon DJ. Yus M. Angew. Chem. Int. Ed.  2005,  44:  1602 
• 9a Cao K. Zhang F. Tu YQ. Zhuo X. Fan CA. Chem. Eur. J.  2009,  15:  6332 
• 9b Xiao F. Chen Y. Liu Y. Wang JB. Tetrahedron  2008,  64:  2755 
• 9c Huang H. Jiang H. Chen K. Liu H. J. Org. Chem.  2009,  74:  5476 
• 9d Guchhait S. Jadeja K. Madaan C. Tetrahedron Lett.  2009,  50:  6861 
• 9e Gaddam V. Ramesh S. Nagarajan R. Tetrahedron  2010,  66:  4218 
• 9f Li X. Mao Z. Wang Y. Chen W. Lin X. Tetrahedron  2011,  3858 
• 10a Dallinger D. Kappe CO. Chem. Rev.  2007,  107:  2563 
• 10b Martínez-Palou R. Mol. Diversity  2006,  10:  435 
• 10c Polshettiwar V. Nadagouda MN. Varma RS. Aust. J. Chem.  2009,  62:  16 
• 11a Forsyth SA. Pringle JM. MacFarlane DR. Aust. J. Chem.  2004,  57:  113 
• 11b Leadbeater NE. Torenius HM. J. Org. Chem.  2002,  67:  3145 
• 11c Hoffmann J. Nüchter M. Ondruschka B. Wasserscheid P. Green Chem.  2003,  5:  296 
• 12 Palimkar SS. Siddiqui SA. Daniel T. Lahoti RJ. Srinivasan KV. J. Org. Chem.  2003,  68:  9373 
• 13a Kumar A. Rao MS. Rao VK. Aust. J. Chem.  2010,  63:  135 
• 13b Kumar A. Rao MS. Rao Ahmad I. Khungar B. Aus. J. Chem.  2009,  62:  322 
• 13c Kumar A. Ahmad I. Rao MS. J. Sulfur Chem.  2009,  30:  570 
• 13d Kumar A. Ahmed I. Rao MS. Can. J. Chem.  2008,  86:  899 
• 13e Kumar A. Jain N. Rana S. Chauhan SMS. Synlett  2004,  2785 
• 15a Kim Y.-J. Streitwieser A. J. Am. Chem. Soc.  2002,  124:  5757 
• 15b Chakraborti AK. Roy SR. J. Am. Chem. Soc.  2009,  131:  6902 
• 15c Chakraborti AK. Roy SR. Kumar D. Chopra P. Green Chem.  2008,  10:  1111 
• 16 Nishio T. Omote Y. J. Chem. Soc., Perkin Trans. 1  1983,  1773 

14

Synthesis of 2,4-Diphenylquinoline (4a)
A mixture of benzaldehyde (106 mg, 1 mmol), aniline (93 mg, 1 mmol), phenylacetylene (102 mg, 1 mmol), and Yb(OTf)₃ (62 mg, 10 mol%) was taken in a tube containing 2 mL of [bmim][BF₄] and placed under MW irradiation in a CEM Discover BenchMate^® reactor. The reaction parameters were set to 80 W, 80 ˚C for 3 min under stirring. After completion of the reaction, the reaction mixture was extracted with EtOAc-hexane (1:1, 3 × 10 mL). Evaporation of solvent gave the crude product which was purified by passing through a silica column to give pure 4a (253 mg, 90%) as an off-white solid; mp 108-110 ˚C (lit.^¹6 109-111 ˚C).