Palladium-catalyzed intramolecular N-arylation of heteroarenes: A novel and efficient route to benzimidazo[1,2-a]quinolines

Journal of Organic Chemistry

Volumn 71, Issue 3, 2006, Pages 1280-1283

  Venkatesh, C ^a   Sundaram, G S M ^a   Ila, H ^a   Junjappa, H ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY KANPUR   (India)

Author keywords

[No Author keywords available]

Indexed keywords

AMINATION; CATALYSTS; PALLADIUM COMPOUNDS; SYNTHESIS (CHEMICAL);

BUCHWALD-HARWTIG ARYL AMINATION; INTRAMOLECULAR N-ARYLATION; QUINOLINES;

NITROGEN COMPOUNDS;

2 (2 BROMOANILINO)QUINOLINE; 2 (2' BROMOANILINO)QUINOLINE; 2 (METHYLSULFONYL)QUINOLINE; 2 (METHYLTHIO)QUINOLINE; 2 CHLORONITROBENZENE; 4 METHYL 2 (METHYLTHIO)QUINOLINE; BENZIMIDAZO[1,2 A]QUINOLINE; BENZIMIDAZO[1,2 F]PHENANTHRIDINE; BENZIMIDAZO[2,1 A]ISOQUINOLINE; BENZOTRIAZOLE DERIVATIVE; INDOLO[2,3 B]QUINOLINE; NITROBENZENE DERIVATIVE; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

AMINATION; ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; ARTICLE; ARYLATION; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE; RING CLOSING METATHESIS; TEMPERATURE DEPENDENCE; TRANQUILIZING ACTIVITY;

BENZIMIDAZOLES; CATALYSIS; CYCLIZATION; ISOQUINOLINES; LIGANDS; MOLECULAR STRUCTURE; PALLADIUM; SOLVENTS; TEMPERATURE;

EID: 32144431909     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0522411     Document Type: Article

References (53)

1. Katritzky, A. R.; Tymoshenko, D. O.; Monteux, D.; Vvedensky, V.; Nikonov, G.; Cooper, C. B.; Deshpande, M. J. Org. Chem. 2000, 65, 8059 and references therein.
2. (a) Maryanoff, B. E.; McComsey, D. F.; Ho, W.; Shank, R. P.; Dubinsky, B. Bioorg. Med. Chem. Lett. 1996, 6, 333.
3. (b) Reitz, A. B.; Gauthier, D. A.; Ho, W.; Maryanoff, B. E. Tetrahedron 2000, 56, 8809 and references therein.
4. (a) Rida, S. M.; Soliman, F. S. G.; Badawey, E.; Kappe, T. J. Heterocycl. Chem. 1988, 25, 1725.
5. (b) Rida, S. M.; Soliman, F. S. G.; Badawey, E.; El-Ghazzawi, E.; Kader, O.; Kappe, T. J. Heterocycl. Chem. 1988, 25, 1087.
6. Badawey, E.; Kappe, T. Eur. J. Med. Chem. 1995, 30, 327.
7. El-Hawash, S. A. M.; Badawey, E.; Kappe, T. Pharmazie 1999, 54, 341.
8. Pastor, J.; Siro, J. G.; Garcio-Navio, J. L.; Vaquero, J. J.; Alvarez-Builla, J.; Gago, F.; de Pascual-Teresa, B.; Pastor, M.; Melia Rodrigo, M. J. Org. Chem. 1997, 62, 5476 and references therein.
9. Panda, K.; Suresh, J. R.; Ila, H.; Junjappa, H. J. Org. Chem. 2003, 68, 3498.
10. (a) Popov, I. I. Khim. Geterotsikl. Soedin. 1989, 1695.
11. (b) Kuzmenko, V. V.; Komissarov, V. N.; Simonov, A. M. Khim. Geterotsikl. Soedin. 1981, 1497.
12. (c) Bergerat, I.; Galous, H.; Rabaron, A.; Combet-Farnoux, C.; Miocque, M. J. Heterocycl Chem. 1985, 22, 369.
13. (d) Toth, G.; Kovacs, A.; Balogh, M.; Hermecz, J. J. Heterocycl. Chem. 1991, 28, 497.
14. (a) Cooper, G.; Irwin, W. J. J. Chem. Soc., Perkin Trans, 1, 1976, 75.
15. (b) Grimshaw, J.; Trocha-Grimshaw, J. Tetrahedron Lett. 1975, 2601.
16. (c) Benincori, T.; Sannicolo, F. J. Heterocycl. Chem. 1988, 25, 1029.
17. (d) Tkach, I. I.; Luk'yanets, E. A. Khim. Geterosikl. Soedin. 1992, 1053;
18. Chem. Abstr. 1993, 119, 28058z.
19. (e) Knolker, H.-J.; Boese, R.; Hitzemann, R. Chem. Ber. 1990, 123, 327.
20. (f) Alajarin, M.; Vidal, A.; Tovar, F. Tetrahedron Lett. 2000, 41, 7029.
21. (g) Ohta, S.; Yuasa, T.; Narita, Y.; Kawasaki, I.; Minamii, E.; Yamashita, M. Heterocycles 1991, 32, 1923.
22. (h) Alajarin, M.; Vidal, A.; Tovar, F.; Conesa, C. Tetrahedron Lett. 1999, 40, 6127.
23. Review: Tennant, G. In The Chemistry of Heterocyclic Compounds; Weissberger, A., Taylor, E. C., Eds.; Interscience Publishers: NewYork, 1980; Vol. 40, Part 2, p 257.
24. (a) Baklanov, M. V.; Frolov, A. N. Zh. Org. Khim. 1991, 27, 638.
25. (b) Prostakov, N. S.; Varlamov, A. V.; Shendrik, I. V.; Anisimov, B. N.; Krapivko, A. P.; Lavani-Edogiaverie, S.; Fomichev, A. A. Khim. Geterotsikl. Soedin. 1983, 1384;
26. Chem. Abstr. 1984, 100, 51481y.
27. Hubert, A. J. J. Chem. Soc. C 1969, 1334.
28. (a) Pipe, D. F.; Rees, C. W. J. Chem. Soc., Chem. Commun. 1982, 520.
29. (b) Houghton, P. G.; Pipe, D. F.; Rees, C. W. J. Chem. Soc., Perkin Trans, 1 1985, 1471.
30. (a) Anderson, D. J.; Taylor, A. J. J. Heterocycl. Chem. 1986, 23, 1091.
31. (b) Morgan, G. T.; Stewart, J. Chem. Ind. 1937, 670.
32. (c) Stephensop, L.; Warburton, W. K. J. Chem. Soc. C 1970, 1355.
33. Review: Ila, H.; Junjappa, H.; Mohanta, P. K. Progress in Heterocyclic Chemistry; Gribble, G. W., Gilchrist, T. L., Eds.; Pergamon: New York, 2001; Vol. 13, Chapter 1, p 1.
34. (a) Venkatesh, C.; Singh, B.; Mahata, P. K.; Ila, H.; Junjappa, H. Org. Lett. 2005, 7, 2169.
35. (b) Mahata, P. K.; Venkatesh, C.; Syam Kumar, U. K.; Ila, H.; Junjappa, H. J. Org. Chem. 2003, 68, 3966.
36. (a) Panda, K.; Venkatesh, C.; Ila, H.; Junjappa, H. Eur. J. Org. Chem. 2005, 2045.
37. (b) Sundaram, G. S. M.; Venkatesh, C.; Syamkumar, U. K.; Ila, H.; Junjappa, H. J. Org. Chem. 2004, 69, 5760.
38. (c) Peruncheralathan, S.; Khan, T. A.; Ila, H.; Junjappa, H. Tetrahedron 2004, 60, 3457.
39. Evindar, G.; Batey, R. A. Org. Lett. 2003, 5, 133.
40. Reviews: (a) Muci, A. R.; Buchwald, S. L. Top. Curr. Chem. 2002, 219, 131.
41. (b) Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805.
42. (c) Hartwig, J. F. Acc. Chem. Res. 1998, 31, 852.
43. Recent papers: (a) Ferreira, I. C. F. R.; Queiroz, M.-J. R. P.; Kirsch, G. Tetrahedron 2003, 59, 975.
44. (b) Jonckers, T. H. M.; Maes, B. U. W.; Lemiere, G. L. F.; Rombouts, G.; Pieters, L.; Haemers, A.; Dommisse, R. A. Synlett 2003, 615.
45. (c) Bedford, R. B.; Cazin, C. S. J. Chem. Commun. 2002, 2310.
46. Panda, K.; Siddiqui, I.; Mahata, P. K.; Ila, H.; Junjappa, H. Synlett 2004, 449.
47. Jones, G. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.: Pergamon Press: Oxford, 1996; Vol. 5, Chapter 5.05, p 167.
48. Only one report has recently appeared for this kind of cyclization involving Pd-catalyzed one-pot tandem inter- and intramolecular Buchwald-Hartwig animation of 2-chloro-3-iodopyridine with aminoazines and diazines to give dipyrido[1,2-a:3́,2́-d]imidazole and its benzo and aza analogues: Loones, K. T. J.; Maes, B. U. W.; Dommisse, R. A.; Lemiere, G. L. F. Chem. Commun. 2004, 2466.
49. Iwaki, T.; Yashuhara, A.; Sakamoto, T. J. Chem. Soc., Perkin Trans. 1 1999, 1505.
50. Chezal, J. M.; Moreau, E.; Delmas, G.; Gueiffier, A.; Blache, Y.; Grassy, G.; Lartigue, C.; Chavignon, O.; Teulade, J. C. J. Org. Chem. 2001, 66, 6576.
51. (a) Coulson, D. R. Inorg. Synth. 1972, 13, 121.
52. (b) Darnault, G.; Saquet, M.; Thuillier, A. Chim. Ind. 1983, 10, 391.
53. (c) Taylor, E. C.; Chittenden, M. L.; Martin, S. F. Heterocycles 1973, 7, 59.