General and regioselective synthesis of substituted pyrroles by metal-catalyzed or spontaneous cycloisomerization of (Z)-(2-en-4-ynyl)amines

Journal of Organic Chemistry

Volumn 68, Issue 20, 2003, Pages 7853-7861

  Gabriele, Bartolo ^a   Salerno, Giuseppe ^a   Fazio, Alessia ^a  

^a UNIVERSITY OF CALABRIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSTS; CHEMICAL BONDS; ISOMERIZATION;

PYRROLES;

AROMATIC COMPOUNDS;

ALKENYL GROUP; ALKYL GROUP; AMINE; COPPER CHLORIDE; METAL; PHENYL GROUP; PYRROLE DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL BOND; CHEMICAL STRUCTURE; CYCLIZATION; ISOMERISM; MOLECULAR STABILITY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0141431058     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034850j     Document Type: Article

References (76)

1. (a) Comprehensive Heterocyclic Chemistry; Bird, C. W., Ed.; Pergamon Press: Oxford, 1996; Vol. 2
2. For some recent examples on biological activity of pyrrole derivatives, see: (b) Micheli, F.; Di Fabio, R.; Cavanni, P.; Rimland, J. M.; Capelli, A. M. ; Chiamulera, C.; Corsi, M.; Corti, C.; Donati, D.; Feriani, A.; Ferraguti, F.; Maffeis, M.; Missio, A.; Ratti, E.; Paio, A.; Pachera, R.; Quartaroli, M.; Reggiani, A.; Sabbatini, F. M.; Trist, D. G.; Ugolini, A.; Vitulli, G. Bioorg. Med. Chem. 2003, 11, 171-183.
3. (c) Mach, R. H.; Huang, Y. S.; Freeman, R. A.; Wu, L.; Blair, S.; Luedtke, R. R. Bioorg. Med. Chem. 2003, 11, 225-233.
4. (d) Bleicher, K. H.; Wuthrich, Y.; Adam, G.; Hoffmann, T.; Sleight, A. J. Bioorg. Med. Chem. Lett. 2002, 12, 3073-3076.
5. (e) Hackling, A. E.; Stark, H. ChemBioChem 2002, 3, 946-961.
6. (f) El-Gaby M. S. A.; Gaber, A. M.; Atalla, A. A.; Al-Wahab, K. A. A. Farmaco 2002, 57, 613-617.
7. (g) Silvestri, R.; De Martino, G.; Artico, M.; La Regina, G.; Ragno, R.; Loddo, R.; La Colla, P.; Marongiu, M. E.; La Colla, M.; Pani, A. Med. Chem. Res. 2002, 11, 195-218.
8. (h) Yanagimoto, K.; Lee, K. G.; Ochi, H.; Shibamoto, T. J. Agric. Food Chem. 2002, 50, 5480-5484.
9. (i) Bergauer, M.; Hubner, H.; Gmeiner, P. Bioorg. Med. Chem. Lett. 2002, 12, 1937-1940.
10. (j) Di Santo, R.; Costi, R.; Artico, M.; Ragno, R.; Massa, S.; La Colla, M.; Loddo, R.; La Colla, P.; Pani, A. Med. Chem. Res. 2002, 11, 153-167.
11. (k) Borthwick, A. D.; Crame, A. J.; Ertl, P. F.; Exall, A. M.; Haley, T. M.; Hart, G. J.; Mason, A. M.; Pennell, A. M. K.; Singh, O. M. P.; Weingarten, G. G.; Woolven, J. M. J. Med. Chem. 2002, 45, 1-18.
12. (l) Sessler, J. L.; Kral, V.; Shishkanova, T. V.; Gale, P. A. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 4848-4853.
13. (m) Lee, H.; Lee, J.; Lee, S.; Shin, Y.; Jung, W. H.; Kim, J. H.; Park, K.; Kim, K.; Cho, H. S.; Ro, S.; Lee, S.; Jeong, S.; Choi, T.; Chung, H. H.; Koh, J. S. Bioorg. Med. Chem. Lett. 2001, 11, 3069-3072.
14. (n) Andreani, A.; Cavalli, A.; Granaiola, M.; Guardigli, M.; Leoni, A.; Locatelli, A.; Morigi, R.; Rambaldi, M.; Recanatini, M.; Roda, A. J. Med. Chem. 2001, 44, 4011-4014.
15. (o) Brower, J. O.; Lightner, D. A.; McDonagh, A. F. Tetrahedron 2001, 57, 7813-7828.
16. (p) Furstner, A.; Grabowski, E. J. ChemBioChem 2001, 2, 706-709.
17. (q) Seki, M.; Mori, K. Eur. J. Org. Chem. 2001, 503-506.
18. (r) White, C. M.; Satz, A. L.; Bruice, T. C.; Beerman, T. A. Proc. Natl. Acad. Sci. U.S.A. 2001, 98, 10590-10595.
19. (s) Hidalgo, F. J.; Alaiz, M.; Zamora, R. Chem. Res. Toxicol. 2001, 14, 582-588.
20. For a recent review on conjugated polymers incorporating the pyrrole unit, see: (a) Higgins, S. Chem. Soc. Rev. 1997, 26, 247-257
21. For some recent examples on the use of pyrrole derivatives in material science see: (b) Ogawa, K.; Rasmussen, R. C. J. Org. Chem. 2003, 68, 2921-2928.
22. (c) Naji, A.; Cretin, M.; Persin, M.; Sarrazin, J. J. Membr. Sci. 2003, 212, 1-11.
23. (d) Chen, J.; Too, C. O.; Wallace, G. G.; Swiegers, G. F.; Skelton, B. W.; White, A. H. Electrochim. Acta 2002, 47, 4227-4238.
24. (e) Zotti, G.; Zecchin, S.; Schiavon, G.; Berlin, A. Chem. Mater. 2002, 14, 3607-3614.
25. (f) Glidle, A.; Swann, M. J.; Hadyoon, C. S.; Cui, L.; Davis, J.; Ryder, K. S.; Cooper, J. M. J. Electron. Spectrosc. 2001, 121, 131-148.
26. (g) Pleus, S.; Schulte, B. J. Solid State Electrochem. 2001, 5, 522-530.
27. (h) Korri-Youssoufi, H.; Makrouf, B.; Yassar, A. Mater. Sci. Eng., C 2001, 15, 265-268.
28. (i) Gale, P. A.; Bleasdale, E. R.; Chen, G. Z. Supramol. Chem. 2001, 13, 557-563.
29. (j) Costello, B. P. J. D.; Evans, P.; Guernion, N.; Ratcliffe, N. M.; Sivanand, P. S.; Teare, G. C. Synth. Met. 2001, 118, 199-200.
30. (k) Chou, S. S. P.; Yeh, Y. H. Tetrahedron Lett. 2001, 42, 1309-1311.
31. (l) Tietze, L. F.; Kettschau, G.; Heuschert, U.; Nordmann, G. Chem. Eur. J. 2001, 7, 368-373.
32. For a review on recent advances in the synthesis of pyrroles, see: (a) Ferreira, V. F.; de Souza, M. C. V. B.; Cunha, A. C.; Pereira, L. O. R.; Ferreira, M. L. G. Org. Prep. Proced. Int. 2001, 33, 411-454.
33. For a recent review on synthesis of aromatic heterocycles, see: (b) Gilchrist, T. L. J. Chem. Soc., Perkin Trans. 1 2001, 2491-2515.
34. For some very recent examples on the synthesis of pyrrole derivatives, see: (c) Trofimov, B. A.; Demenev, A. P.; Sobenina, L. N.; Mikhaleva, A. I.; Tarasova, O. A. Tetrahedron Lett. 2003, 44, 3501-3503.
35. (d) Ranu, B. C.; Dey, S. S. Tetrahedron Lett. 2003, 44, 2865-2868.
36. (e) Zhang, X. Q.; Sui, Z. Tetrahedron Lett. 2003, 44, 3071-3073.
37. (f) Quiclet-Sire, B.; Quintero, L.; Sanchez-Jimenez, G.; Zard, S. Z. Synlett 2003, 75-78.
38. (g) Kim J. T.; Kel'in A. V.; Gevorgyan, V. Angew. Chem., Int. Ed. 2003, 42, 98-101.
39. (h) Okada, H.; Akaki, T.; Oderaotoshi, Y.; Minakata, S.; Komatsu, M. Tetrahedron 2003, 59, 197-205.
40. (i) Bullington, J. L.; Wolff, R. R.; Jackson, P. F. J. Org. Chem. 2002, 67, 9439-9442.
41. (j) Demir, A. S.; Akhmedov, D. M.; Sesenoglu, O. Tetrahedron 2002, 58, 9793-9799.
42. (k) Langer, P.; Freifeld, I. Chem. Commun. 2002, 2268-2269.
43. (l) Deng, G. S.; Jiang, N.; Ma, Z. H.; Wang, J. B. Synlett 2002, 1913-1915.
44. (m) Attanasi, O. A.; De Crescentini, L.; Favi, G.; Filippone, P.; Mantellini, F.; Santeusanio, S. J. Org. Chem. 2002, 67, 8178-8181.
45. (n) Bergman, J.; Rehn, S. Tetrahedron 2002, 58, 9175-9185.
46. (o) Smith, N. D.; Huang, D. H.; Cosford, N. D. P. Org. Lett. 2002, 4, 3537-3539.
47. (p) Quiclet-Sire, B.; Wendeborn, F.; Zard, S. Z. Chem. Commun. 2002, 2214-2215.
48. (q) Hwang, S. H.; Kurth, M. J. J. Org. Chem. 2002, 67, 6564-6567.
49. (r) Paulus, O.; Alcaraz, G.; Vaultier, M. Eur. J. Org. Chem. 2002, 2565-2572.
50. (s) Pedrosa, R.; Andres, C.; de las Heras, L.; Nieto, J. Org. Lett. 2002, 4, 2513-2516.
51. (t) Dvornikova, E.; Kamienska-Trela, K. Synlett 2002, 1152-1154.
52. (u) Airaksinen, A. J.; Ahlgren, M.; Vepsalainen, J. J. Org. Chem. 2002, 67, 5019-5021.
53. (v) Gabriele, B.; Salerno, G.; Fazio, A.; Campana, F. B. Chem. Commun. 2002, 1408-1409.
54. (w) Hewton, C. E.; Kimber, M. C.; Taylor, D. K. Tetrahedron Lett. 2002, 43, 3199-3201.
55. (x) Just, P. E.; Chane-Ching, K. I.; Lacaze, P. C. Tetrahedron 2002, 58, 3467-3472.
56. (y) Hercouet, A.; Neu, A.; Peyronel, J. F.; Carboni, B. Synlett 2002, 829-831.
57. (z) Alickmann, D.; Frohlich, R.; Maulitz, A. H.; Wurthwein, E. U. Eur. J. Org. Chem. 2002, 1523-1537.
58. Gabriele, B.; Salerno, G.; Lauria, E. J. Org. Chem. 1999, 64, 7687-7692.
59. Gabriele, B.; Salerno, G.; Fazio, A. Org. Lett. 2000, 2, 351-352.
60. Gabriele, B.; Salerno, G.; Fazio, A.; Pittelli, R. Tetrahedron 2003, 59, 6251-6259.
61. Gabriele, B.; Salerno, G.; Fazio, A.; Bossio, M. R. Tetrahedron Lett. 2001, 42, 1339-1341.
62. 3N/DMA), has been recently reported: Kel'in, A. V.; Sromek, A. W.; Gevorgyan, V. J. Am. Chem. Soc. 2001, 123, 2074-2075.
63. Shannon, R. D.; Prewitt, C. T. Acta Crystallogr. 1969, B25, 925-946.
64. Mitsunobu, O. Synthesis 1981, 1-28.
65. Marshall, J. A.; DuBay, W. J. J. Org. Chem. 1993, 58, 3435-3443.
66. Denis, J. N.; Greene, A. E.; Serra, A. A.; Luche, M. J. J. Org. Chem. 1986, 51, 46-50.
67. (a) Duboudin, J. G.; Jousseaume, B. J. Organomet. Chem. 1979, 168, 1-11.
68. (b) Duboudin, J. G.; Jousseaume, B.; Bonakdar, A. J. Organomet. Chem. 1979, 168, 227-232.
69. Alami, M.; Ferri, F.; Linstrumelle, G. Tetrahedron Lett. 1993, 34, 6403-6406.
70. Nussbaumer, P.; Petranyi, G.; Stültz, A. J. Med. Chem. 1991, 34, 65-73.
71. Hegedus, L. S.; McKearin, J. M. J. Am. Chem. Soc. 1982, 104, 2444-2451.
72. Seiller, B.; Bruneau, C.; Dixneuf, P. H. Tetrahedron 1995, 51, 13089-13102.
73. Martin, S. F.; Li, W. J. Org. Chem. 1991, 56, 642-650.
74. Qian, C.; Huang, T. J. Organomet. Chem. 1997, 548, 143-147.
75. Marshall, J. A.; Xie, S. J. Org. Chem. 1995, 60, 7230-7237.
76. Ueda, Y.; Chuang, J. M.; Crast, L. B.; Partyka, R. A. J. Org. Chem. 1988, 53, 5107-5113.