Copper(II)-catalyzed synthesis of benzo[ f ]pyrido[1,2- a ]indole-6,11-dione derivatives via naphthoquinone difunctionalization reaction

Journal of Organic Chemistry

Volumn 77, Issue 2, 2012, Pages 1191-1197

  Liu, Yun ^a   Sun, Jin Wei ^a  

^a JIANGSU NORMAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

1 ,3-DICARBONYL COMPOUNDS; 1 ,4-NAPHTHOQUINONE; CATALYZED SYNTHESIS; DIFUNCTIONALIZATION; HIGH YIELD; INTRAMOLECULAR CYCLIZATIONS; ISOQUINOLINES; NAPHTHOQUINONE; OXIDATIVE AROMATIZATION; REACTION MECHANISM; THREE COMPONENT REACTIONS;

BROMINE COMPOUNDS; CATALYSIS; COPPER; KETONES; SYNTHESIS (CHEMICAL);

CYCLIZATION;

12 (2 NAPHTHOYL) 2 METHYLBENZO[F]PYRIDO[1,2 A]INDOLE 6,11 DIONE; 12 (2 NAPHTHOYL)BENZO[F]PYRIDO[1,2 A]INDOLE 6,11 DIONE; 12 (4 CHLOROBENZOYL) 2 ETHYLBENZO[F]PYRIDO[1,2 A]INDOLE 6,11 DIONE; 12 (4 CHLOROBENZOYL) 2 METHYLBENZO[F]PYRIDO[1,2 A]INDOLE 6,11 DIONE; 12 (4 CHLOROBENZOYL)BENZO[F]PYRIDO[1,2 A]INDOLE 6,11 DIONE; 12 (4 METHOXYBENZOYL) 2 ETHYLBENZO[F]PYRIDO[1,2 A]INDOLE 6,11 DIONE; 12 (4 METHOXYBENZOYL) 2 METHYLBENZO[F]PYRIDO[1,2 A]INDOLE 6,11 DIONE; 12 (4 METHOXYBENZOYL)BENZO[F]PYRIDO[1,2 A]INDOLE 6,11 DIONE; 12 (BIPHENYLCARBONYL) 2 ETHYLBENZO[F]PYRIDO[1,2 A]INDOLE 6,11 DIONE; 12 (BIPHENYLCARBONYL) 2 METHYLBENZO[F]PYRIDO[1,2 A]INDOLE 6,11 DIONE; 12 (BIPHENYLCARBONYL)BENZO[F]PYRIDO[1,2 A]INDOLE 6,11 DIONE; 12 BENZOYL 2 ETHYLBENZO[F]PYRIDO[1,2 A]INDOLE 6,11 DIONE; 12 BENZOYL 2 METHYLBENZO[F]PYRIDO[1,2 A]INDOLE 6,11 DIONE; 12 BENZOYLBENZO[F]PYRIDO[1,2 A]INDOLE 6,11 DIONE; 12 ETHOXYCARBONYL 2 ETHYLBENZO[F]PYRIDO[1,2 A]INDOLE 6,11 DIONE; 12 ETHOXYCARBONYL 2 METHYLBENZO[F]PYRIDO[1,2 A]INDOLE 6,11 DIONE; 12 ETHOXYCARBONYLBENZO[F]PYRIDO[1,2 A]INDOLE 6,11 DIONE; 12 METHOXYCARBONYL 2 ETHYLBENZO[F]PYRIDO[1,2 A]INDOLE 6,11 DIONE; 12 METHOXYCARBONYL 2 METHYLBENZO[F]PYRIDO[1,2 A]INDOLE 6,11 DIONE; 12 METHOXYCARBONYLBENZO[F]PYRIDO[1,2 A]INDOLE 6,11 DIONE; 14 (4 CHLOROBENZOYL)BENZ[5,6]INDOLO[2,1 A]ISOQUINOLINE 8,13 DIONE; 14 (4 METHOXYBENZOYL)BENZ[5,6]INDOLO[2,1 A]ISOQUINOLINE 8,13 DIONE; 14 BENZOYLBENZ[5,6]INDOLO[2,1 A]ISOQUINOLINE 8,13 DIONE; 14 ETHOXYCARBONYLBENZ[5,6]INDOLO[2,1 A]ISOQUINOLINE 8,13 DIONE; 14 METHOXYCARBONYLBENZ[5,6]INDOLO[2,1 A]ISOQUINOLINE 8,13 DIONE; BENZO[F]PYRIDO[1,2 A]INDOLE 6,11 DIONE DERIVATIVE; COPPER; INDOLE DERIVATIVE; NAPHTHOQUINONE; UNCLASSIFIED DRUG;

AROMATIZATION; ARTICLE; CATALYSIS; CHEMICAL REACTION; CYCLIZATION; DIFUNCTIONALIZATION REACTION; SYNTHESIS;

EID: 84862940994     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo2023312     Document Type: Article

References (48)

1. Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Eds.; Pergamon Press: Oxford, 1984; Vols. 1-8.
2. Flitsch, W. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Pergamon: Oxford, 1996; Vol. 8, p 237.
3. Swinbourne, F. J.; Hunt, J. H.; Klinkert, G. Adv. Heterocycl. Chem. 1979, 23, 103
4. Shipman, M. Sci. Synth. 2001, 10, 745
5. Sriran, D.; Yogeeswari, P.; Thirumurugan, R.; Bal, T. R. Nat. Prod. Res. 2005, 19, 393
6. Valencia, E.; Freyer, A. J.; Shamma, M. Tetrahedron Lett. 1984, 25, 599
7. Alonso, R.; Castedo, L.; Dominguez, D. Tetrahedron Lett. 1985, 26, 2925
8. Gundersen, L.-L.; Charnock, C.; Negussie, A. H.; Rise, F.; Teklu, S. Eur. J. Pharm. Sci. 2007, 30, 26
9. Hagishita, S.; Yamada, M.; Shirahase, K.; Okada, T.; Murakami, Y.; Ito, Y.; Matsuura, T.; Wada, M.; Kato, T.; Ueno, M.; Chikazawa, Y.; Yamada, K.; Ono, T.; Teshirogi, I.; Ohtani, M. J. Med. Chem. 1996, 39, 3636
10. Chai, W.; Breitenbucher, J. G.; Kwok, A.; Li, X.; Wong, V.; Carruthers, N. I.; Lovenberg, T. W.; Mazur, C.; Wilson, S. J.; Axe, F. U.; Jones, T. K. Bioorg. Med. Chem. Lett. 2003, 13, 1767
11. Bermudez, J.; Fake, C. S.; Joiner, G. F.; Joiner, K. A.; Km, F. D.; Miner, W. D.; Sanger, G. J. J. Med. Chem. 1990, 33, 1924
12. Weide, T.; Arve, L.; Prinz, H.; Waldmann, H.; Kessler, H. Bioorg. Med. Chem. Lett. 2006, 16, 59
13. Nasir, A. I.; Gundersen, L.-L.; Rise, F.; Antonsen, Ø.; Kristensen, T.; Langhelle, B.; Bast, A.; Custers, I.; Haenen, G.; Wikström, H. Bioorg. Med. Chem. Lett. 1998, 8, 1829
14. Hagishita, S.; Yamada, M.; Shirahase, K.; Okada, T.; Murakami, Y.; Ito, Y.; Matsuura, T.; Wada, M.; Kato, T.; Ueno, M.; Chikazawa, Y.; Yamada, K.; Ono, T.; Teshirogi, I.; Ohtani, M. J. Med. Chem. 1996, 39, 3636
15. Humphires, M. J.; Matsumoto, K.; White, S. L.; Olden, K. Cancer Res. 1986, 46, 5215
16. Ostrander, G. K.; Scribner, N. K.; Rohrschneider, L. R. Cancer Res. 1988, 48, 1091
17. Bols, M.; Lillelund, V. H.; Jensen, H. H.; Liang, X. Chem. Rev. 2002, 102, 515
18. Gubin, J.; de Vogelaer, H.; Inion, H.; Houben, C.; Lucchetti, J.; Mahaux, J.; Rosseels, G.; Peiren, M.; Clinet, M.; Polster, P.; Chatelain, P. J. Med. Chem. 1993, 36, 1425
19. Clive, D. L. J.; Coltart, D. M.; Zhou, Y. J. Org. Chem. 1999, 64, 1447
20. Chatelain, P.; Laruel, A.; Beaufort, P.; Meysmans, L.; Clinet, M. Cardioscience 1992, 3, 117
21. Ruprecht, R. M.; Mullaney, S.; Andersen, J.; Bronson, R. J. Acquired Immune Defic. Syndr. 1989, 2, 149
22. Gruters, R. A.; Neefjes, J. J.; Tersmette, M.; de Goede, R. E.; Tulp, A.; Huisman, H. G.; Miedema, F.; Ploegh, H. L. Nature 1987, 330, 74
23. Kaspas, A.; Fleet, G. W. J.; Dwek, R. A.; Petursson, S.; Namgoong, S. K.; Ramsden, N. G.; Jacob, G. S.; Radamacher, T. W. Proc. Natl. Acad. Sci. U. S. A. 1989, 86
24. Østby, O. B.; Dalhus, B.; Gundersen, L.-L.; Rise, F.; Bast, A.; Haenen, G. R. M. M. Eur. J. Org. Chem. 2000, 3763
25. Gundersen, L.-L.; Malterud, K. E.; Negussie, A. H.; Rise, F.; Teklu, S.; Ostby, O. B. Bioorg. Med. Chem. 2003, 11, 5409
26. Teklu, S.; Gundersen, L.-L.; Larsen, T.; Malterud, K. E.; Rise, F. Bioorg. Med. Chem. 2005, 13, 3127
27. Saeva, F. D.; Luss, H. R. J. Org. Chem. 1988, 53, 1804
28. Fletetcher, G. L.; Bender, S. L.; Wadsworth, D. H. U.S. Patent 4,577,024, 1986
29. Chem. Abstr. 1984, 100, 122772.
30. Sonnenschein, H.; Henrich, G.; Resch-Genger, V.; Schulz, B. Dyes Pigm. 2000, 46, 23
31. Vlahovici, A.; Andrei, M.; Druta, I. J. Lumin. 2002, 96, 279
32. Vlahovici, A.; Druta, I.; Andrei, M.; Cotlet, M. J. Lumin. 1999, 82, 155
33. Mitsumori, T.; Bendikov, M.; Dautel, O.; Wudl, F.; Shioya, T.; Sato, H.; Sato, Y. J. Am. Chem. Soc. 2004, 126, 16793
34. Shen, Y.-M.; Grampp, G.; Leesakul, N.; Hu, H.-W.; Xu, J.-H. Eur. J. Org. Chem. 2007, 3718
35. Pratt, E. F.; Luckenbaugh, R. W.; Erickson, R. L. J. Org. Chem. 1954, 19, 178
36. Pratt, E. F.; Rice, R. G.; Luckenbaugh, R. W. J. Am. Chem. Soc. 1957, 79, 1212
37. Citterio, A.; Fochi, M.; Marion, A.; Mele, A.; Sebastiano, R.; Delcanale, M. Heterocycles 1998, 48, 1993
38. Liu, Y.; Hu, H.-Y.; Liu, Q.-J.; Hu, H.-W.; Xu, J.-H. Tetrahedron 2007, 63, 2024
39. Labinger, J. A.; Bercaw, J. E. Nature 2002, 417, 507
40. Davies, H. M. L.; Manning, J. R. Nature 2008, 451, 417
41. Wendlandt, A. E.; Suess, A. M.; Stahl, S. S. Angew. Chem., Int. Ed. 2011, 50, 11062
42. Gamez, P.; Aubel, P. G.; Driessen, W. L.; Reedijk, J. Chem. Soc. Rev. 2001, 30, 376
43. Liu, Y.; Hu, H.-Y.; Zhang, Y.; Hu, H.-W.; Xu, J.-H. Org. Biomol. Chem. 2010, 8, 4921
44. Liu, Y.; Zhang, Y.; Shen, Y.-M.; Hu, H.-W.; Xu, J.-H. Org. Biomol. Chem. 2010, 8, 2449
45. Similar oxidative additions of pyridine to naphthoquinone to give the same 1,4-naphthoquinone-2-pyridinium salt are known to take place in the presence of such oxidants as iodine and manganese dioxide(17) or air.(18) Citterio, A.; Fochi, M.; Maronati, A.; Sebastiano, R.; Mele, A. Synthesis 1997, 614
46. Schmidt, A.; Topp, M.; Mordhorst, T.; Schneider, O. Tetrahedron 2007, 63, 1842
47. Lin, C.-Y.; Cheng, Y.-C.; Tsai, A.-I.; Chuang, C.-P. Org. Biomol. Chem. 2006, 4, 1097
48. Jiang, M.-C.; Chuang, C.-P. J. Org. Chem. 2000, 65, 5409