Synthesis of quinolines and fused pyridocoumarins from N-propargylanilines or propargylaminocoumarins by catalysis with gold nanoparticles supported on TiO2

Tetrahedron

Volumn 69, Issue 23, 2013, Pages 4612-4616

  Symeonidis, Theodoros S ^a   Lykakis, Ioannis N ^a   Litinas, Konstantinos E ^a  

^a ARISTOTLE UNIVERSITY OF THESSALONIKI   (Greece)

Author keywords

6 Propargylaminocoumarins; Fused dipyridocoumarins; Gold nanoparticles; Heterogeneous catalysis; N Propargylanilines; Pyrido 5,6 coumarins; Quinolines

Indexed keywords

ALUMINUM OXIDE; AMINOCOUMARIN DERIVATIVE; ANILINE DERIVATIVE; COUMARIN DERIVATIVE; GOLD NANOPARTICLE; N PROPARGYLANILINE DERIVATIVE; PROPARGYLAMINOCOUMARIN DERIVATIVE; PYRIDOCOUMARIN DERIVATIVE; QUINOLINE DERIVATIVE; TITANIUM DIOXIDE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL BOND; CHEMICAL MODIFICATION; CHEMICAL REACTION; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS; REPRODUCIBILITY;

EID: 84876964557     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2013.04.026     Document Type: Article

References (85)

1. G. Jones A.R. Katritzky, C.W. Rees, Comprehensive Heterocyclic Chemistry Vol. 2 1984 Pergamon Oxford, U.K. 395 510 Chapter 2.08
2. A.R. Katritzky Handbook of Heterocyclic Chemistry 1985 Pergamon Oxford, U.K.
3. T. Eicher, and S. Hauptmann The Chemistry of Heterocycles 1995 Thieme Stuttgart, Germany 316
4. D.S. Coffey, S.A. May, and A.M. Ratz G.W. Gribble, T.L. Gilchrist, Progress in Heterocyclic Chemistry Vol. XIII 2001 Pergamon London, U. K. 238 260
5. V. Kouznetsov, L.Y.V. Mendez, and C.M.M. Gomez Curr. Org. Chem. 9 2005 141
6. J.P. Michael Nat. Prod. Rep. 24 2007 223
7. A. Hassner, and C. Stumer Organic Syntheses Based on Name Reactions and Unnamed Reactions 1994 Pergamon Oxford, U.K.
8. L. Kurti, and B. Czako Strategic Applications of Named Reactions in Organic Synthesis 2005 Elsevier Academic Burlington, MA
9. R.H.F. Mansake, and M. Kulka Org. React. 7 1953 59
10. C.-C. Cheng, and S.-J. Yan Org. React. 28 1982 37
11. J. Marco-Contelles, E. Perez-Mayoral, A. Samadi, M. do Carmo Carreiras, and E. Soriano Chem. Rev. 109 2009 2652
12. F.W. Bergstrom Chem. Rev. 35 1944 153
13. R.H. Reitsema Chem. Rev. 43 1948 47
14. X. Zhang, T. Yao, M.A. Campo, and R.C. Larock Tetrahedron 66 2010 1177
15. M. Jida, and B. Deprez New J. Chem. 36 2012 869
16. Che, C.-M.; So, M.-H. US Patent 2011/0282065 A1, 2011.
17. A. Kulkarni, and B. Torok Green Chem. 12 2010 875
18. D.H. Murray, J. Mendez, and S.A. Brown The Natural Coumarins: Occurrence, Chemistry and Biochemistry 1982 J. Wiley & Sons New York, NY
19. R. O'Kennedy, and R.D. Thornes Coumarins: Biology, Applications and Mode of Action 1997 J. Wiley & Sons Chichester, UK
20. K.C. Fylaktakidou, D.J. Hadjipavlou-Litina, K.E. Litinas, and D.N. Nicolaides Curr. Pharm. Des. 10 2004 3813
21. F. Dall'Acqua, and D. Vedaldi W.M. Horspool, P.S. Song, CRC Handbook of Organic Photochemistry and Photobiology 1995 CRC Boca Raton, FL 1341 1350
22. L. Santana, E. Uriarte, F. Roleira, N. Milhazes, and F. Borges Curr. Med. Chem. 11 2004 3239
23. M.V. Kulkarni, G.M. Kulkarni, C.-H. Lin, and C.-M. Sun Curr. Med. Chem. 13 2006 2795
24. T.K. Mandal, V.V. Kuznetsov, and A.T. Soldatenkov Chem. Heterocycl. Comp. 30 1994 867
25. K. Ukawa, T. Ishiguro, Y. Wada, and A. Nohara Heterocycles 24 1986 1931
26. D. Heber Arch. Pharmacol. 320 1987 402
27. D. Heber, and T. Berghaus J. Heterocycl. Chem. 31 1994 1353
28. I.A. Khan, M.V. Kulkarni, M. Gopal, M.S. Shahabuddin, and C.-M. Sun Bioorg. Med. Chem. Lett. 15 2005 3584
29. K.J. Liska, A.F. Fentiman, and R.L. Foltz Tetrahedron Lett. 11 1970 4657
30. V. Petrow, and E.L. Rewald J. Chem. Soc. 1949 769
31. S.D. Joshi, V.D. Sakhardande, and S. Seshadri Indian J. Chem. 23B 1984 206
32. V.V. Mulwad, and M.B. Dalvi Indian J. Chem., Sect. B 42 2003 358
33. D. Heber, I.C. Ivanov, and S.K. Karagiosov J. Heterocycl. Chem. 32 1995 505
34. C.K. Ghosh, A. Ray, and A. Patra J. Heterocycl. Chem. 38 2001 1459
35. K.C. Majumdar, I. Ansary, S. Samanta, and B. Roy Tetrahedron Lett. 52 2011 411
36. D.R. Gautam, J. Protopappas, K.C. Fylaktakidou, K.E. Litinas, D.N. Nicolaides, and C.A. Tsoleridis Tetrahedron Lett. 50 2009 448
37. T.S. Symeonidis, M.G. Kallitsakis, and K.E. Litinas Tetrahedron Lett. 52 2011 5452
38. K.C. Majumdar, R.K. Nandi, S. Ganai, and A. Taher Synlett 2011 116
39. S.M. Sethna, and R. Phadke Org. React. 7 1953 1
40. D.P. Ahuja, K.K. Chakravarti, and S. Siddiqui J. Sci. Ind. Res. 9B 1950 187
41. Chem. Abstr. 1951, 45, 7125e
42. E. Galariniotou, V. Fragos, A. Makri, K.E. Litinas, and D.N. Nicolaides Tetrahedron 63 2007 8298
43. S. Fajgelj, L. Golic, B. Stanovnik, and M. Tisler Heterocycles 37 1994 847
44. G.J. Hutchings, M. Brust, and H. Schmidbaur Chem. Soc. Rev. 37 2008 1759 and references cited therein
45. K. Saha, S.S. Agasti, C. Kim, X. Li, and V.M. Rotello Chem. Rev. 112 2012 2739
46. H. Jans, and Q. Huo Chem. Soc. Rev. 41 2012 2849
47. E.C. Dreaden, A.M. Alkilany, X. Huang, C.J. Murphy, and M.A. El-Sayed Chem. Soc. Rev. 41 2012 2740
48. R.A. Sperling, P.R. Gil, F. Zhang, M. Zanella, and W. Parak J. Chem. Soc. Rev. 37 2008 1896
49. R. Wilson Chem. Soc. Rev. 37 2008 2028
50. M. Stratakis, and H. Garcia Chem. Rev. 112 2012 4469
51. C. Della Pina, E. Falletta, and M. Rossi Chem. Soc. Rev. 41 2012 350
52. L. Lili, Z. Xin, G. Jinsen, and X. Chunming Green Chem. 14 2012 1710
53. A. Noujima, T. Mitsudome, T. Mizugaki, K. Jitsukawa, and K. Kaneda Molecules 16 2011 8209
54. M. Kidwai, V. Bansal, A. Kumar, and S. Mozumdar Green Chem. 9 2007 742
55. M.J. Oila, and A.M.P. Koskinen ARKIVOC XV 2006 76
56. Y.-W. Lin, C.-C. Huang, and H.-T. Chang Analyst 136 2011 863
57. D. Liu, Z. Wang, and X. Jiang Nanoscale 3 2011 1421
58. C. Wu, F. Liu, and F. Ko Anal. Bioanal. Chem. 399 2011 103
59. S. Kegnaes, J. Mielby, U.V. Mentzel, C.H. Christensen, and A. Riisager Green Chem. 12 2010 437
60. A. Grirrane, A. Gorma, and H. Garcia J. Catal. 264 2009 138
61. G.J. Hutchings Catal. Today 138 2008 9
62. C. Della Pina, E. Falletta, L. Prati, and M. Rossi Chem. Soc. Rev. 37 2008 2077
63. A. Corma, and H. Garcia Chem. Soc. Rev. 37 2008 2096
64. X. Zhang, and A. Corma Angew. Chem., Int. Ed. 47 2008 4358
65. M. Turner, V.B. Golovko, O.P. Vaughan, P. Abdulkin, A. Berenguer-Marcia, M.S. Tikhov, B.F. Johnson, and R.M. Lambert Nature 454 2008 981
66. C. Gryparis, C. Efe, C. Raptis, I.N. Lykakis, and M. Stratakis Org. Lett. 14 2012 2956
67. I.N. Lykakis, A. Psyllaki, and M. Stratakis J. Am. Chem. Soc. 133 2011 10426
68. C. Efe, I.N. Lykakis, and M. Stratakis Chem. Commun. 2011 803
69. Y.-S. Hon, T.-W. Tseng, and C.-Y. Cheng Chem. Commun. 2009 5618
70. B.B. Dey, and M.N. Goswami J. Chem. Soc. 115 1919 531
71. J. Hashim, T.N. Glasnov, J.M. Kremsner, and C.O. Kappe J. Org. Chem. 71 2006 1707
72. N. De Kimpe, and M. Keppens Tetrahedron 52 1996 3705
73. N. Shakya, K.K. Roy, and A.K. Saxena Bioorg. Med. Chem. 17 2009 830
74. A. Sahin, O. Cakmak, I. Demirtas, S. Okten, and A. Tutar Tetrahedron 64 2008 10068
75. C.S. Cho, B.H. Oh, and S.C. Shim J. Heterocycl. Chem. 36 1999 1175
76. R.A. Seibert, T.R. Norton, A.A. Benson, and F.W. Bergstrom J. Am. Chem. Soc. 68 1946 2721
77. P.J. Amal Joseph, S. Priyadarshini, M. Lakshmi Kantam, and H. Maheswaran Tetrahedron Lett. 53 2012 1511
78. M.T. Barros, S.S. Dey, C.D. Maycock, and P. Rodrigues Tetrahedron 68 2012 6263
79. A. Correa, I. Tellitu, E. Dominguez, and R. SanMartin J. Org. Chem. 71 2006 8316
80. B. Schmidt, S. Krehl, and E. Jablowski Org. Biomol. Chem. 10 2012 5119
81. A. Carta, M. Loriga, G. Paglietti, M. Ferrone, M. Fermeglia, S. Pricl, T. Sanna, C. Ibba, P. La Colla, and L. Loddo Bioorg. Med. Chem. 15 2007 1914
82. R.S. Menon, A.D. Findlay, A.C. Bissember, and M.G. Banwell J. Org. Chem. 74 2009 8901
83. A. Furstner, and P.W. Davies Angew. Chem., Int. Ed. 46 2007 3410
84. C. Nevado, and A.M. Echavarren Chem. - Eur. J. 11 2005 3155
85. M.T. Reetz, and K. Sommer Eur. J. Org. Chem. 2003 3485