Lewis acid catalyzed Nenitzescu indole synthesis

Journal of Heterocyclic Chemistry

Volumn 43, Issue 4, 2006, Pages 873-879

  Velezheva, Valeriya S ^a   Kornienko, Albert G ^c   Topilin, Sergey V ^c   Turashev, Ascar D ^c   Peregudov, Alexander S ^c   Brennan, Patrick J ^b  

^a A N NESMEYANOV INSTITUTE OF ORGANOELEMENT COMPOUNDS   (Russian Federation)

^b Department of Environmental and Radiological Health Sciences   (United States)

^c NONE

Author keywords

[No Author keywords available]

Indexed keywords

1,4 BENZOQUINONE; 5 HYDROXYINDOLE; ENAMINE; INDOLE DERIVATIVE; LEWIS ACID;

ARTICLE; BIOLOGICAL ACTIVITY; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 33747396903     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570430410     Document Type: Article

References (51)

1. H. Y. Meltzer, Neuropsychopharmacology, 21, 106 (1999);
2. B. E. Leonard, CNS Drugs, 4, 1 (1995);
3. T. C. R. Vijayalaxmi, C. R. Thomas, J. R. Reiter and S. H. Terence, J. Clin. Oncol., 20, 2575 (2002);
4. S. Kaneko, K. Okumura, Y. Numaguchi , H. Matsui, K. Murase, S. Mokuno, I. Morishima, K. Hira, Y. Toki, T. Ito and T. Hayakawa. Life Sciences, 67, 101 (2000).
5. R. D. E. Sewell, in "Introduction to the Principles of Drug Design and Action", H. J. Smith ed.; Harwood Academic Publishers, Amsterdam, B.V., 1998, pp 391-410.
6. T. A. Gus'kova, Pharmaceutical Chemistry Journal, 35, 527 (2001), Springer Verlag New York;
7. J. A. McCullers, Expert Opin, on Investigational Drugs, 14, 305 (2005),
8. Ashley Publications; R. G. Glushkov, T. A. Gu'skova, Pharm. Chem. J. (Engl. Trans.), 33, 115 (1999),
9. D. Wang, Y. U. De Sheng, F. Qin, L. Fang and P. Gong, Chinese Chem. Lett., 15, 19 (2004).
10. Y. Leblanc, W. C. Black, C.-C. Chan, S. Charleson, D. Delorme, D. Denis, C. Bayly, J. Y. Gauthier, R. Grimm, R. Gordon, D. Guay, P. Hamel, S. Kargman, C. K. Lau, J. Mancini, M. Ouellet, D. Percival, P. Roy, K. Skorey, P. Tagari, P. Vickers, E. Wong, L. Xu and P. Prasit, Bioorg. Med. Chem. Lett., 6, 731 (1996).
11. A. Roller, O. K. Bahr, J. Streffer, S. Winter, M. Heneka, M. Deininger, R. Meyermann, U. Naumann, E. Gulbins and M. Weller, Biochem. and Biophys. Res. Comm., 259, 600 (1999).
12. A. R. Maguire, S. J. Plunkett, S. Papot, M. Clynes, R. O' Connor and S. Touhey, Bioorg. Med. Chem., 9, 745 (2001).
13. R. M. Philips, M. A. Naylor, M. Jaffar, S. W. Doughty, S. A. Everett, A. G. Breen, G. A. Choudry and I. J. Stratford, J. Med. Chem., 42, 4071 (1999).
14. J. M. Pawlak, V. V. Khau, D. R. Hutchinson and M. J. Martinelli, J. Org. Chem., 61, 9055 (1996).
15. B. Dotzauer and R. Troschutz, Synlett. 1039 (2004).
16. H. D. Beall, S. Winski, E. Swann, A. R. Hudnott, A. S. Cotteril, N. O'Sullivan, S. J. Green, R. Bien, D. Siegel, D. Ross and C. J. Moody, J. Med. Chem., 41, 4755 (1998).
17. T. M. Bohme, C. E. Augelli-Szafran, H. Hallak, T. Pugsley, K. Serpa and R. D. Schwarz, J. Med. Chem., 45, 3094 (2002).
18. M. A. Naylor, M. Jaffar, J. Nolan, M. A. Stephens, S. Butler, K. B. Patel, S. A. Everett, G. E. Adams and I. J. Stratford, J. Med. Chem., 40, 2335 (1997).
19. R. J. Sundberg, in Indoles. Best synthetic methods series. Academic Press, New York, pp 54-63 (1996);
20. N. N. Suvorov, V. G. Avramenko, V. N. Shkilkova and L. I. Zamyshlyaeva, British Patent 1.174.034 (1968); Chem. Abstr., 66814m (1970).
21. G. R. Allen, in Org. React., 1973, 20, pp 337-454.
22. D. M. Ketcha, L. J. Wilson and D. E. Portlock, Tetrahedron Lett., 41, 6253 (2000).
23. M. Kinugawa, H. Arai, H. Nishikawa, A. Sakaguchi, T. Ogasa, S. Tomioka, M. Kasai, J. Chem. Soc., Perkin Trans. 1, 2677 (1995).
24. J. B. Patrick and E. K. Saunders, Tetrahedron Lett., 20, 4009 (1979).
25. E. K. Panisheva, L. M. Alekseeva, A. S. Shashkov, V. G. Granik, Chem. Heterocycl. Comp. (Russ.), 8, 1164 (2003).
26. G. Domschke, J. Prakt. Chem., 311, 807 (1969).
27. T. A. Engler and J. Wanner, Tetrahedron Lett., 38, 6135 (1997);
28. T. A. Engler, K. O. Lynch, W. Chai and S. P. Meduna, Tetrahedron Lett., 36, 2713 (1995);
29. T. A. Engler, M. A. Letavic, R. Iyengar, K. O. LaTessa and J. P. Reddy, J. Org. Chem., 64, 2391 (1999).
30. U. Kucklander, Tetrahedron., 29, 921 (1973).
31. V. I. Shvedov, E. K. Panisheva, T. F. Vlasova and A. N. Grinev, J. Gen. Chem. USSR (Engl. Trans.), 9, 1225 (1973).
32. G. S. Gadaginamath, R. R. Kavali and S. R. Pujar, Synthetic Comm., 33, 2285 (2003).
33. J. J. Li, in Name Reactions: A Collection of Detailed Reaction Mechanisms, Springer, Berlin, 2002, p. 255.
34. E. Bernatek and T. Ledaal, Acta Chem. Scand., 12, 2053 (1958).
35. J. R. Allen, Jr. C. Pidacks, and M. J. Weiss, J. Am. Chem. Soc., 88, 2536 (1966).
36. E. Knoevenagel, E. Reinecke, Chem. Ber., 32, 423 (1899).
37. M. C. Bagley; J. W. Dale, J. W. Bower, Synlett, 1149 (2001).
38. R. Moehlau, Chem. Ber., 27, 3377 (1894).
39. S. Coffey, J. K. Thomson, F. J. Wilson, J. Chem. Soc., 856 (1936).
40. J. Decombe, Ann. Chim., 18, 81 (1932).
41. M. C. Bagley, C. Brace, J. W. Dale, M. Ohnesorge, N. G.; Phillips, X. Xiong, J. Bower, J. Chem. Soc. Perkin Trans. 1, 14, 1663 (2002).
42. C. Goldschmidt, Chem. Ber., 29, 105 (1896).
43. J-P. Celerier, E. L. Deloisy, G. Hommet, P. Maitte, J. Org. Chem., 44, 3089 (1979).
44. B. Singh, G. Y. Lesher, J. Heterocyclic Chem., 27, 2085 (1990).
45. A. P. Terent'ev, E. A. Viktorova, B. M. Eselson, A. N. Kost, V. V. Ershov, J. Gen. Chem. USSR (Engl. Transl.), 30, 2402 (1960).
46. G. R. Cook, L. G. Beholz, J. R. Stille, J. Org. Chem., 59, 3575 (1994).
47. A. D. Garnovskii, V. L. Abramenko, J. Gen. Chem. USSR (Engl. Transl.), 55, 1630 (1985).
48. A. N. Grinev, V. N. Ermakova, I. A. Mel'nikova, A. P. Terent'ev, J. Gen. Chem. USSR (Engl. Transl.), 31, 2146 (1961).
49. A. N. Kost, L. G. Iudin, E. J. Zinchenko, Chem. Heterocycl. Compd. (Engl. Transl.), 9, 306 (1973).
50. A. N. Grinev, V. N. Ermakova, A. P. Terent'ev, J. Gen. Chem. USSR (Engl. Transl.), 32, 1928 (1962).
51. H. L. Mc. Pherson, B. V. Ponder, J. Heterocyclic Chem., 15, 43 (1978).