Mild and Convenient Synthesis of 1,2‐Dihydroquinolines from Anilines and Acetone Catalyzed by Ytterbium(III) Triflate in Ionic Liquids

References

• Yoshimura , M. , Fujii , T. , Inoue , K. , Umehara , M. and Nagasaki , H. Process for producing 2,2,4‐trimethyl‐1,2‐dihydroquinoline . U.S. patent 4,746,743 . 1988 .
   Google Scholar
• Bower , J. S. Process for the preparation of 2,2,4‐trimethyl‐1,2‐dihydro quinoline compounds . U.S. patent 4,514,570 . 1985 .
   Google Scholar
• Gibba , C. F. and Falls , C. Dihydroquinoline condensation product . U.S. patent 2,400,500 . 1946 .
   Google Scholar
• Bickhoff , E. M. , Livingston , A. L. , Guggolz , J. and Thompson , C. R. 1954 . Quinoline derivatives as antioxidants for carotene . J. Agric. Food Chem. , 2 : 1229 – 1231 .
   Google Scholar
• Weber , H. and Shuttleworth , L. Mixture on cyan and yellow dyes to form a green hue for color filter array element . U.S. patent 5,147,844 . 1992 .
   Google Scholar
• Zhi , L. , Tegley , C. M. and Kallel , E. A. 1998 . 5‐Aryl‐1,2‐dihydrochromeno [3,4‐f]quinolines: A novel class of nonsteroidal human progesterone receptor agonists . J. Med. Chem. , 41 : 291 – 303 .
   PubMed Web of Science ®Google Scholar
• Edwards , J. P. , West , S. J. , Marschke , K. B. , Mais , D. E. , Gottardis , M. M. and Jones , T. K. 1998 . 5‐Aryl‐1,2‐dihydro‐5H‐chromeno [3,4‐f]quinolines as potent, orally active, nonsteroidal progesterone receptor agonists: The effect of d‐ring substituents . J. Med. Chem. , 41 : 303 – 310 .
   PubMed Web of Science ®Google Scholar
• Hamann , L. G. , Higuchi , R. I. , Zhi , L. , Edwards , J. P. , Wang , X.‐N. , Marschke , K. B. , Kong , J. W. , Farmer , L. J. and Jones , T. K. 1998 . Synthesis and biological activity of a novel series of nonsteroidal, peripherally selective androgen receptor antagonists derived from 1,2‐dihydropyridono[5,6‐g]quinolines . J. Med. Chem. , 41 : 623 – 639 .
   PubMed Web of Science ®Google Scholar
• Masakatsuu , Y. and Takeo , F. Masakito U. Process for producing 2,2,4‐trimethyl‐1,2‐dihydroquinoline . U.S. patent 4,746,743 . 1988 .
   Google Scholar
• Huma , H. Z. S. , Halder , R. , Kalra , S. S. , Das , J. and Iqbal , J. 2002 . Cu(I)‐catalyzed three‐component coupling protocol for the synthesis of quinoline derivatives . Tetrahedron Lett. , 43 : 6485 – 6488 .
   Web of Science ®Google Scholar
• Wang , M.‐X. , Liu , Y. and Huang , Z.‐T. 2001 . Novel and convenient synthesis of polyfunctionalized quinolines, quinolones and their annulation reactions . Tetrahedron Lett. , 42 : 2553 – 2555 .
   Web of Science ®Google Scholar
• Arisawa , M. , Theeralandanon , C. , Nishida , A. and Nakagawa , M. 2001 . Synthesis of substituted 1,2‐dihydroquinolines and quinolines using ene–ene metathesis and ene–enol ether metathesis . Tetrahedron Lett. , 42 : 8029 – 8033 .
   Google Scholar
• Theoclitou , M.‐E. and Robinson , L. A. 2002 . Novel facile synthesis of 2,2,4 substituted 1,2‐dihydroquinolines via a modified Skraup reaction . Tetrahedron Lett. , 43 : 3907 – 3910 .
   Web of Science ®Google Scholar
• Ranu , B. C. , Hajra , A. and Jana , U. 2000 . Microwave‐assisted simple synthesis of quinolines from anilines and alkyl vinyl ketones on the surface of silica gel in the presence of indium(III) chloride . Tetrahedron Lett. , 41 : 531 – 533 .
   Web of Science ®Google Scholar
• Craig , D. 1938 . The reaction of acetone with aniline . J. Am. Chem. Soc. , 60 : 1458 – 1465 .
   Google Scholar
• Rivora , H. M. Novel apparatus for the obtention of substitution 1,2‐dihydroquinolines . U.S. patent 3,907,507, 1975 .
   Google Scholar
• Yoshimura , M. , Fujii , T. , Inoue , K. , Umehara , M. and Nagasaki , H. Process for producing 2,2,4‐trimethyl‐dihydroquinoline . U.S. patent 4,746,743 . 1988 .
   Google Scholar
• Ambrus , D. , Bar , V. , Manczinger , J. and Matyas , J. 2,2,4‐Trimethyl‐1,2‐dihydro quinoline . Hung. Patent 157,370 . 1970 . Chem. Abstr. 1970, 73, 45371v
   Google Scholar
• Kobayashi , S. , Sugiura , M. , Kitagawa , H. and Lam , W. W.‐L. 2002 . Rare‐earth metal triflates in organic synthesis . Chem. Rev. , 102 : 2227 – 2302 .
   PubMed Web of Science ®Google Scholar
• Kobayashi , S. 1991 . Lanthanide trifluoromethanesulfonate as stable Lewis acid in aqueous media: Yb(OTf)3 catalyzed hydroxymethylation reaction of silyl enol ethers with commercial formaldehyde solution . Chem. Lett. , : 2187 – 2190 .
   Google Scholar
• Kobayashi , S. , Ishitani , H. , Komiyama , S. , Onicin , D. C. and Katritzky , A. R. 1996 . A novel Mannich‐type reaction: Lanthanide triflate–catalyzed reactions of N‐(α‐aminoalkyl)benzotriazoles with silyl enolates . Tetrahedron Lett. , 37 : 3731 – 3734 .
   Google Scholar
• Kotsuki , H. and Arimura , K. 1997 . Yb(OTf)3‐catalyzed Michael addition reactions of β‐ketoesters on silica gel supports and at high pressure . Tetrahedron Lett. , 38 : 7583 – 7586 .
   Google Scholar
• Kobayashi , S. , Hachiya , I. , Takahori , T. , Araki , T. and Ishitani , H. 1992 . Lanthanide trifluoromethanesulfonates as reusable catalysts: Michael and Diels–Alder reactions . Tetrahedron Lett. , 33 : 6815 – 6518 .
   Web of Science ®Google Scholar
• Bromidge , S. , Wilson , P. C. and Whiting , A. 1998 . A parallel combinatorial approach to locating homochiral Lewis acid catalysts for the asymmetric aza‐Diels–Alder reaction of an imino dienophile . Tetrahedron Lett. , 39 : 8905 – 8908 .
   Google Scholar
• Saito , T. , Kawamura , M. and Nishimura , J. 1997 . Ytterbium triflate–catalyzed asymmetric hetero Diels–Alder cycloaddition of a 1‐thiabuta‐1,3‐diene with a chiral N‐acryloyloxazolidinone dienophile: Diastereoface control by solvents or achiral additives . Tetrahedron Lett. , 38 : 3231 – 3234 .
   Google Scholar
• Gothelf , K. V. , Hazell , R. G. and Jorgensen , K. A. 1996 . Control of diastereo‐ and enantioselectivity in metal‐catalyzed 1,3‐dipolar cycloaddition reactions of nitrones with alkenes: Experimental and theoretical investigations . J. Org. Chem. , 61 : 346 – 355 .
   Web of Science ®Google Scholar
• Kobayashi , S. and Nagagama , S. 1998 . A microencapsulated Lewis acid: A new type of polymer‐supported Lewis acid catalyst of wide utility in organic synthesis . J. Am. Chem. Soc. , 120 : 2985 – 2986 .
   Google Scholar
• Thomas , W. 1999 . Room‐temperature ionic liquids: Solvents for synthesis and catalysis . Chem. Rev. , 99 : 2071 – 2083 .
   PubMed Web of Science ®Google Scholar
• Welton , T. 2004 . Ionic liquids in catalysis . Coord. Chem. Rev. , 248 : 2459 – 2477 .
   Web of Science ®Google Scholar
• Su , W.‐K. , Wu , C.‐L. and Su , H. 2005 . Ytterbium(III) trifluoromethanesulfonate catalysed Friedel‐Crafts acylation of 1‐methylpyrrole in ionic liquid . J. Chem. Res., Synop. , 1 : 67 – 68 .
   Google Scholar
• Ross , J. and Xiao , J.‐L. 2002 . Friedel–Crafts acylation reactions using metal triflates in ionic liquid . Green Chem. , 4 : 129
   Web of Science ®Google Scholar
• Anjaiah , S. , Chandrasekhar , S. and Grée , R. 2004 . Carbon–Ferrier rearrangements in ionic liquids using Yb(OTf)3 as catalyst . J. Mol. Cat. , 214A : 133 – 136 .
   Google Scholar
• Bonhote , P. , Dias , A.‐P. , Papageorgiou , N. , Kalyanasundaram , K. and Gratzel , M. 1996 . Hydrophobic, highly conductive ambient‐temperature molten salts . Inorg. Chem. , 35 : 1168 – 1178 .
   PubMed Web of Science ®Google Scholar
• Suarez , P. A. Z. , Dullius , J. E. L. , Einloft , S. , Souza , R. F. D. and Dupont , J. 1996 . The use of new ionic liquids in two‐phase catalytic hydrogenation reaction by rhodium complexes . Polyhedron , 15 : 1217 – 1219 .
   Web of Science ®Google Scholar
• Brindaban , C. R. , Alakananda , H. and Suvendu , S. D. 2003 . Efficient microwave‐assisted synthesis of quinolines and dihydroquinolines under solvent‐free conditions . Tetrahedron , 59 : 813 – 819 .
   Google Scholar
• Layer , R. W. and Son , P.‐N. Mixture containing plastics and decahydroquinolines . Ger. Offen , 2,726,713, 1977; Chem. Abstr. 1977, 88, 122203f
   Google Scholar
• Nekipelova , T. D. , Kurkovskaya , L. N. , Levina , I. I. , Shishkov , V. S. and Kuzmin , V. A. 2001 . Studies of photoinduced addition of water and alcohols to substituted dihydroquinolines . Russ. Chem. Bull. , 50 : 673 – 677 .
   Google Scholar
• Johnson , J. V. , Rauckman , B. S. , Baccanari , D. P. and Roth , B. 1989 . 2,4‐Diamino‐5‐benzylpyrimidines and analogs as antibacterial agents, 12: 1,2‐Dihydroquinolylmethyl analogs with high activity and specificity for bacterial dihydrofolate reductase . J. Med. Chem. , 32 : 1942 – 1949 .
   PubMed Web of Science ®Google Scholar