Copper-catalyzed tandem reaction of isocyanides with N-(2-haloaryl) propiolamides for the synthesis of pyrrolo[3,2-c]quinolin-4-ones

Journal of Organic Chemistry

Volumn 76, Issue 13, 2011, Pages 5346-5353

  Zhou, Fengtao ^a   Liu, Jianguang ^a   Ding, Ke ^a   Liu, Jinsong ^a   Cai, Qian ^a  

^a GUANGZHOU INSTITUTES OF BIOMEDICINE AND HEALTH   (China)

Author keywords

[No Author keywords available]

Indexed keywords

C-C BOND FORMATION; CYCLOADDITION REACTION; EFFICIENT METHOD; FUSED PYRROLE; INTRAMOLECULAR TRAPPING; ISOCYANIDES; TANDEM REACTION; TRIPLE BONDS;

CATALYSIS; COPPER; CYANIDES; CYCLOADDITION; REACTION INTERMEDIATES;

SYNTHESIS (CHEMICAL);

AMIDE; CARBON; COPPER; CYANIDE; ISOCYANIDE DERIVATIVE; N (2 HALOARYL)PROPIOLAMIDE; PYRROLE DERIVATIVE; PYRROLO[3,2 C]QUINOLIN 4 ONE; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; COPPER CATALYZED TANDEM REACTION; CYCLOADDITION; SYNTHESIS;

4-QUINOLONES; AMIDES; CATALYSIS; COPPER; CYANIDES; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 79959670148     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo2006939     Document Type: Article

References (52)

1. For some recent important reviews, see: Gulevich, A. V.; Zhdanko, A. G.; Orru, R. V. A.; Nenajdenko, V. G. Chem. Rev. 2010, 110, 5235
2. Lygin, A. V.; de Meijere, A. Angew. Chem., Int. Ed. 2010, 49, 9094
3. Dömling, A. Chem. Rev. 2006, 106, 17
4. Dömling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168
5. Schöllkopf, U.; Gerhart, F. Angew. Chem., Int. Ed. 1968, 7, 805
6. Schöllkopf, U. Angew. Chem., Int. Ed. 1977, 16, 339
7. For representative examples of transition metal-catalyzed reaction of isocyanides, see: Takaya, H.; Kojima, S.; Murahashi, S. Org. Lett. 2001, 3, 421 (Rh)
8. Motoyama, Y.; Kawakami, H.; Shimozono, K.; Aoki, K.; Nishiyama, H. Organometallics 2002, 21, 3408 (Pt, Rh)
9. Ito, Y.; Sawamura, M.; Hayashi, T. J. Am. Chem. Soc. 1986, 108, 6405 (Au)
10. Sawamura, M.; Hamashima, H.; Ito, Y. J. Org. Chem. 1990, 55, 5935 (Ag)
11. For representative copper-catalyzed reaction of isocyanides, see: Lygin, A. V.; Larionov, O. V.; Korotkov, V. S.; de Meijere, A. Chem.-Eur. J. 2009, 15, 227
12. Bonin, M.-A.; Giguère, D.; Roy, R. Tetrahedron 2007, 63, 4912
13. Kanazawa, C.; Kamijo, S.; Yamamoto, Y. J. Am. Chem. Soc. 2006, 128, 10662
14. Benito-Garagorri, D.; Bocokić, V.; Kirchner, K. Tetrahedron Lett. 2006, 47, 8641
15. Larionov, O. V.; de Meijere, A. Angew. Chem., Int. Ed. 2005, 44, 5664
16. Kamijo, S.; Kanazawa, C.; Yamamoto, Y. J. Am. Chem. Soc. 2005, 127, 9260
17. Ito, Y.; Matsurra, T.; Saegusa, T. Tetrahedron Lett. 1985, 26, 5781
18. Saegusa, T.; Ito, Y.; Kinoshita, H.; Tomita, S. J. Org. Chem. 1971, 36, 3316
19. For a reported example about organocopper intermediates, see: Haglund, O.; Nilsson, M. Synlett 1991, 723
20. For recent reviews about copper-catalyzed coupling reactions, see: Evano, G.; Blanchard, N.; Toumi, M. Chem. Rev. 2008, 108, 3054
21. Monnier, F.; Taillefer, M. Angew. Chem., Int. Ed. 2009, 48, 6954
22. Beletskaya, I. P.; Cheprakov, A. V. Coord. Chem. Rev. 2004, 248, 2337
23. Ma, D.; Cai, Q. Acc. Chem. Res. 2008, 41, 1450
24. Cai, Q.; Zhou, F.; Xu, T.; Fu, L.; Ding, K. Org. Lett. 2011, 13, 340
25. Cai, Q.; Li, Z.; Wei, J.; Fu, L.; Ha, C.; Pei, D.; Ding, K. Org. Lett. 2010, 12, 1500
26. Cai, Q.; Li, Z.; Wei, J.; Ha, C.; Pei, D.; Ding, K. Chem. Commun. 2009, 7581
27. Witherhrup, K. M.; Ransom, R. W.; Graham, A. C.; Bernard, A. M.; Salvatore, M. J.; Lumman, W. C.; Anderson, P. S.; Pitzenberger, S. M.; Varga, S. L. J. Am. Chem. Soc. 1995, 117, 6682
28. For selected total synthesis and some recent synthetic approaches to the Martinelle alkaloids, see: Nieman, J. A.; Ennis, M. D. Org. Lett. 2000, 2, 1395
29. Ma, D.; Xia, C.; Jiang, J.; Zhang, J. Org. Lett. 2001, 3, 2189
30. Snider, B. B.; Ahn, Y.; O'Hare, S. M. Org. Lett. 2001, 3, 4217
31. Powell, D. A.; Batey, R. A. Org. Lett. 2002, 4, 2913
32. Nyerges, M. Heterocycles 2004, 63, 1685
33. Miyata, O.; Shirai, A.; Yoshino, S.; Takeda, Y.; Sugiura, M.; Naito, T. Synlett 2006, 893
34. Ng, P. Y.; Masse, C. E.; Shaw, J. T. Org. Lett. 2006, 8, 3999
35. Hadden, M.; Nieuwenhuyzen, M.; Potts, D.; Stevenson, P. J.; Thompson, N.; Walker, A. D. Tetrahedron 2006, 62, 3977
36. He, Y.; Mahmud, H.; Moningka, R.; Lovely, C. J.; Dias, H. V. R. Tetrahedron 2006, 62, 8755
37. Ikeda, S.; Shibuya, M.; Iwabuchi, Y. Chem. Commun. 2007, 504
38. Zhang, Z.; Zhang, Q.; Yan, Z.; Liu, Q. J. Org. Chem. 2007, 72, 9808
39. Shirai, A.; Miyata, O.; Tohnai, N.; Miyata, M.; Procter, D. J.; Sucunza, D.; Naito, T. J. Org. Chem. 2008, 73, 4464
40. Lovely, C. J.; Badarinarayana, V. Curr. Org. Chem. 2008, 12, 1431
41. Comesse, S.; Sanselme, M.; Daïch, A. J. Org. Chem. 2008, 73, 5566
42. Ueda, M; Kawai, S.; Hayashi, M.; Naito, T.; Miyata, O. J. Org. Chem. 2011, 75, 914
43. Brown, T. H.; Ife, R. J.; Keeling, D. J.; Laing, S. M.; Leach, C. A.; Parsons, M. E.; Price, C. A.; Reavill, D. R.; Wiggall, K. J. J. Med. Chem. 1990, 33, 527
44. Leach, C. A.; Brown, T. H.; Ife, R. J.; Keeling, D. J.; Laing, S. M.; Parsons, M. E.; Price, C. A.; Wiggall, K. J. J. Med. Chem. 1992, 35, 1845
45. Escolano, C.; Jones, K. Tetrahedron Lett. 2000, 41, 8951
46. Helissey, P.; Parrot-Lopez, H.; Renault, J.; Cros, S. E. J. Med. Chem. 1987, 22, 366
47. Wright, G. C.; Watson, E. J.; Ebetino, F. F.; Pals, D. T. J. Med. Chem. 1971, 14, 1060
48. D'Souza, D. M.; Kiel, A.; Herten, D.-P.; Rominger, F.; Müller, T. J. J. Chem.-Eur. J. 2008, 14, 529
49. Kunishima, M.; Kawachi, C.; Morita, J.; Terao, K.; Iwasaki, F.; Tani, S. Tetrahedron 1999, 55, 13159
50. Yanada, R.; Obika, S.; Kobayashi, Y.; Inokuma, T.; Oyama, M.; Yanada, K.; Takemoto, Y. Adv. Synth. Catal. 2005, 347, 1632
51. For details, see the Supporting Information.
52. Ugi, I.; Lohberger, S.; Karl, R. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: New York, 1991; Vol. 2, Part 2, Section 4.6, p 1083.