Synthesis of pyrido[2,3-b]indoles and pyrimidoindoles via Pd-catalyzed amidation and cyclization

Organic and Biomolecular Chemistry

Volumn 10, Issue 26, 2012, Pages 5084-5093

  Kumar, Arepalli Sateesh ^a   Amulya Rao, P V ^a   Nagarajan, Rajagopal ^a  

^a UNIVERSITY OF HYDERABAD   (India)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDATION; CARBOLINES; CORE STRUCTURE; CYCLIZATIONS; DFT CALCULATION; FLUORESCENCE STUDIES; KETO-ENOL TAUTOMERISM; SPECTROSCOPIC TECHNIQUE;

CATALYSIS; DENSITY FUNCTIONAL THEORY; PYRIDINE; QUANTUM YIELD;

CYCLIZATION;

AMIDE; CARBOLINE DERIVATIVE; INDOLE DERIVATIVE; PALLADIUM; PYRIMIDINE DERIVATIVE;

ARTICLE; CHEMISTRY; CYCLIZATION; SYNTHESIS;

AMIDES; CARBOLINES; CYCLIZATION; INDOLES; PALLADIUM; PYRIMIDINES;

EID: 84862567710     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/c2ob25371b     Document Type: Article

References (58)

1. J. Elguero P. Goya N. Jagerovic A. M. S. Silva Targets Heterocycl. Syst. 2002 6 52
2. P. M. Dewick, in Medicinal Natural Products: A Biosynthetic Approach, WILEY, New York, 2nd edn, 2002
3. A. Deiters S. F. Martin Chem. Rev. 2004 104 2199
4. S. Agarwal S. Cämmerer S. Filali W. Fröhner J. Knöll M. P. Krahl K. R. Reddy H.-J. Knölker Curr. Org. Chem. 2005 9 1601
5. R. R. Gataullin Russ. J. Org. Chem. 2008 45 321
6. D. Bolton I. T. Forbes C. J. Hayward D. C. Piper D. R. Thomas M. Thompson N. Upton Bioorg. Med. Chem. Lett. 1993 3 1941
7. B. E. Love Top. Heterocycl. Chem. 2006 2 93
8. U. Somei and A. Basha, in Indole Alkaloids, Hawood Academic Publishers, Amsterdam, 1997
9. G. R. Humphrey J. T. Kuethe Chem. Rev. 2006 106 2875
10. R. J. Sundberg, in Indoles, ed., Academic Press, London, 1996
11. R. J. Sundberg, in Comprehensive Heterocyclic Chemistry II, ed., A. R. Katritzky, C. W. Ress, E. F. V. Scriven, and, C. W. Bird, Pergamon Press, Oxford, U.K., 1996, vol. 2, p. 119
12. N. Helbecque J. L. Berbier J. P. Henichard C. Moquin-Pattey M. Guyot Cancer Biochem. Biophys. 1987 9 271
13. W. Peczyska-Czoch F. Pognan L. Kaczmarek J. Boratynski J. Med. Chem. 1994 37 3503
14. N. N. Pogodaeva V. A. Shagun A. A. Semenov Khim.-Fram. Zh. 1985 19 1054
15. T. Okamoto, T. Akase, S. Izumi, S. Inaba and H. Yamamoto, Japanese patent 7 220 196; Chem. Abstr., 1972, 77, 152142
16. J. Winters and N. Di Mola, West German patent, 2 442 513; Chem. Abstr., 1975, 82, 156255
17. L. Paolini Sci. Rep. Ist. Super. Sanita 1961 1 86
18. J. Winters N. D. Mola Chem. Abstr. 1975 82 156255
19. M. E. Hepperle, J. F. Liu and R. S. Rowland, International Patent Application Publication No. WO/2007/097981, 2007
20. J. Kim K. Shinya K. Furihata Y. Hayakawa H. Seto Tetrahedron Lett. 1997 38 3431
21. D. Ioshida Biochem. Biophys. Res. Commun. 1978 83 915
22. D. Oshida T. Matsumoto Cancer Lett. 1980 10 141
23. S. Okuda M. M. Robinson J. Am. Chem. Soc. 1959 81 740
24. F. Portela-Cubillo B. A. Surgenor R. A. Aitken J. C. Walton J. Org. Chem. 2008 73 8124
25. F. Liger F. Popowycz T. Besson L. Picot C. M. Galmarini B. Joseph Bioorg. Med. Chem. 2007 15 5615
26. A. Okamoto K. Tanaka I. Saito J. Am. Chem. Soc. 2003 125 5066
27. A. Okamoto K. Tanaka I. Saito J. Am. Chem. Soc. 2004 126 9458
28. D. H. H. Showalter J. A. Bridges H. Zhou D. A. Sercel A. McMichael D. W. Fry J. Med. Chem. 1999 42 5464
29. P. J. Barnes K. F. Chung C. P. Page Pharmacol. Rev. 1998 50 515
30. P. H. Howarth Allergy 1995 50 s22 13
31. G. L. Bundy L. S. Banitt P. L. Dobrowoski J. R. Palmer T. M. Schwartz D. C. Zimmermann M. F. Lipton M. A. Mauragis M. F. Veley R. B. Appell R. C. Clouse E. D. Daugs Org. Process Res. Dev. 2001 5 144
32. C. E. Muller U. L. Geis B. Grahner W. Lanzner K. Eger J. Med. Chem. 1996 39 2483
33. C. E. Muller I. Hide J. Daly K. Rothenhausler K. Eger J. Med. Chem. 1990 33 2822
34. J. W. Darrow, G. D. Maynard and R. F. Horvath, International Patent Application Publication No. WO/1999/ 9,951,598, 1999
35. G. Xu L. Zheng S. Wang Q. Dang X. Bai Synlett 2009 19 3206
36. J. M. Cook, M. L.V. Linn and W. Yin, International Patent Application Publication No. US 2009/0306121 A1, 2009
37. J. P. Wolfe S. Wagaw J.-F. Marcoux S. L. Buchwald Acc. Chem. Res. 1998 31 805
38. J. F. Hartwig Angew. Chem., Int. Ed. 1998 37 2046
39. D. S. Surry S. L. Buchwald Angew. Chem., Int. Ed. 2008 47 6338
40. J. F. Hartwig Acc. Chem. Res. 2008 41 1534
41. A. S. Kumar R. Nagarajan Org. Lett. 2011 6 1398
42. V. Gaddam R. Nagarajan J. Org. Chem. 2007 72 3573
43. R. Camps Ber. Dtsch. Chem. Ges. 1899 32 3228
44. D. A. Pflum, Camps cyclization. in Named reactions in heterocyclic chemistry, ed., J. J. Li, and, E. J. Corey, Wiley-Interscience, Hoboken, NJ, 2005, p. 386
45. S. W. Paine A. J. Kresge A. Salam J. Phys. Chem. A 2005 109 4149
46. L. Zhu Bozelli J. Phys. Chem. A 2003 107 3696
47. S. W. Paine A. Salam Chem. Phys. 2006 331 61
48. N. Ple A. Turck A. Heynderickx G. Queguiner J. Heterocycl. Chem. 1994 31 1311
49. E. Erb D. Pocar M. Valle J. Chem. Soc., Perkin Trans. 1 1999 421
50. Y. Kondo R. Watanabe T. Sakamoto H. Yamanak Chem. Pharm. Bull. 1989 37 2933
51. T. Higashino E. Hayashi Heterocycles 1981 15 483
52. Principles of fluorescence spectroscopy, J. R. Lakowicz, Springer Sciences and Business Media, New York, 3rd edn, 2006
53. Springer series on fluorescence: methods and applications, ed., O. S. Wolfbeis, Springer Sciences and Business Media, Berlin, Heidelberg, 2010
54. Topics in fluorescence spectroscopy, ed., J. R. Lakowicz, Kluwer Academic Publishers, New York, 2002, vols. 1-4
55. H. Meier Angew. Chem., Int. Ed. 2005 44 2482
56. A. C. Rimsdale K. L. Chan R. E. Martin P. G. Jokisz A. B. Holmes Chem. Rev. 2009 109 897
57. C. Li M. Liu N. G. Pschirer M. Baumgartner K. Müllen Chem. Rev. 2010 18 4619
58. A. C. Arias J. D. Mackenzie I. McCulloch J. Rivnay A. Salleo Chem. Rev. 2010 110 3