Lewis acid-catalyzed synthesis of functionalized pyrroles

Advanced Synthesis and Catalysis

Volumn 351, Issue 5, 2009, Pages 715-719

  Attanasi, Orazio A ^a   Berretta, Stefano ^a   De Crescentini, Lucia ^a   Favi, Gianfranco ^a   Giorgi, Gianluca ^b   Mantellini, Fabio ^a  

^a UNIVERSITY OF URBINO   (Italy)

^b UNIVERSITY OF SIENA   (Italy)

Author keywords

1,2 diaza 1,3 butadienes; Alkynes; Hydroamination; Lewis acids; Michael addition; Pyrroles

Indexed keywords

EID: 63349107290     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200800807     Document Type: Article

References (56)

1. a) R. J. Sundberg, in: Comprehensive Heterocyclic Chemistry, Vol. 4, (Eds.: A. R. Katritzky, C. W. Rees), Pergamon Press, Oxford, 1984; pp 313-368;
2. b) G. W. Gribble, in: Comprehensive Heterocyclic Chemistry II, Vol. 2, (Eds.: A. R. Katritzky, C. W. Rees, E. F. V. Scriven), Pergamon-Elsevier Science Amsterdam, 1996, Chapter 4;
3. c) C. Rochais, V. Lisowski, P. Dallemagne, S. Rault, Bioorg. Med. Chem. 2006, 14, 8162-8175;
4. d) R. Di Santo, R. Costi, M. Artico, G. Miele, A. Lavecchia, E. Novellino, A. Bergamini, R. Cancio, G. Maga, ChemMedChem 2006, 1, 1367-1378;
5. e) L. Zeng, E. W. Miller, A. Pralle, E. Y. Isacoff, C. J. Chang, J. Am. Chem. Soc. 2006, 128, 10-11.
6. E. T. Pelkey, J. S. Russel, in: Progress in Heterocyclic Chemistry, Vol. 19, (Eds.: G. W. Gribble, J. A. Joule), Elsevier, Oxford, 2008, pp 135-175.
7. a) L. Knorr, Ber. dtsch. chem. Ges. 1884, 17, 1635;
8. b) L. Knorr, H. Lange, Ber. dtsch. ehem. Ges. 1902, 35, 2998. For recent examples:
9. c) J. M. Manley, M. J. Kalman, M. J. Conway, C. C. Ball, J. L. Havens, R. J. Vaidyanathan, J. Org. Chem. 2003, 68, 6447-6750;
10. d) C. M. Shiner, T. D. Laner, Tetrahedron 2005, 61, 11628-11640.
11. a) A. Hantzsch, Ber. dtsch. ehem. Ges. 1890, 23, 1474. For recent examples:
12. b) V. S. Matiychuk, R. L. Martyack, N. D. Obushak, Y. V. Ostapiuk, N. I. Pidlypnyi, Chem. Heterocycl. Compd. 2004, 40, 1218-1219.
13. a) L. Knorr, Ber. dtsch. chem. Ges. 1885, 18, 299;
14. b) C. Paal, Ber. dtsch. ehem. Ges. 1885, 18, 367. For recent examples:
15. c) J. Chen, H. Wu, Z. Zheng, C. Jin, X. Zhang, W. Su, Tetrahedron Lett. 2006, 47, 5383-5387;
16. d) G. Minetto, L. F. Raveglia, A. Sega, M. Tiddei, Eur. J. Org. Chem. 2005, 5277-5288.
17. Recent examples: a) I. Nakamura, Y. Yamamoto, Chem. Rev. 2004, 104, 2127-2198;
18. b) D. J. S. Cyr, B. A. Arndtsen, J. Am. Chem. Soc. 2007, 129, 12366-12367;
19. c) S. Chiba, Y.-F. Wang, G. Lapointe, K. Narasaka, Org. Lett. 2008, 10, 313-316;
20. d) X.-T. Liu, L. Huang, F.-J. Zheng, Z.-P Zhan, Adv. Synth. Catal. 2008, 350, 2778-2788;
21. e) Y. Lu, X. Fu, H. Chen, X. Du, X. Jia, Y. Liu, Adv. Synth. Catal. 2009, 351, 129-134.
22. Recent examples: a) G. Balme, Angew. Chem. 2004, 116, 6396-6399;
23. Angew. Chem. Int. Ed. 2004, 43, 6238-6241;
24. b) D: Tejedor, D. Gonzales-Cruz, F. Garcia-Tellado, J. J. Marrero-Tellado, M. L. Rodriguez, J. Am. Chem. Soc. 2004, 126, 8390-8391;
25. c) Y. Yamamoto, H. Hayashi, T. Saigoku, H. Nishiyama, J. Am. Chem. Soc. 2005, 127, 10804-10805;
26. d) O. V. Larionov, A. Meijere, Angew. Chem. 2005, 117, 5809-5813;
27. Angew. Chem. Int. Ed. 2005, 44, 5664-5667.
28. a) O. A. Attanasi, P. Bonifazi, E. Foresti, G. Pradella, J. Org. Chem. 1982, 47, 684-687;
29. b) O. A. Attanasi, P. Filippone, Synlett 1997, 1128-1140;
30. c) O. A. Attanasi, L. De Crescentini, G. Favi, P. Filippone, F. Mantellini, S. Santeusanio, J. Org. Chem. 2002, 67, 8178-8181;
31. d) O. A. Attanasi, L. De Crescentini, G. Favi, P. Filippone, F. Mantellini, S. Santeusanio, J. Org. Chem. 2004, 69, 2686-2692.
32. a) O. A. Attanasi, G. Favi, P. Filippone, S. Lillini, F. Mantellini, D. Spinelli, M. Stenta, Adv. Synth. Catal. 2007, 349, 907-915;
33. b) A. Schmidt, V. Karapetyan, O. A. Attanasi, G. Favi, S. Görl, F. Mantellini, P. Langer, Synlett 2007, 2965-2968;
34. c) V. Karapetyan, S. Mkrtchyan, A. Schmidt, O. A. Attanasi, G. Favi, F. Mantellini, A. Villinger, C. Fischer, P. Langer, Adv. Synth. Catal. 2008, 350, 1331-1336;
35. d) O. A. Attanasi, G. Favi, P. Filippone, G. Giorgi, F. Mantellini, G. Moscatelli, D. Spinelli, Org. Lett. 2008, 10, 1983-1986.
36. a) J. B. Hendrickson, R. Rees, J. Am. Chem. Soc. 1961, 83, 1250-1251;
37. b) D. S. James, P. E. Fanta, J. Org. Chem. 1962, 27, 3346-3348;
38. c) J. B. Hendrickson, R. Rees, J. F. Templeton, J. Am. Chem. Soc. 1964, 86, 107-111;
39. d) S. K. Khetan, J. G. Hiriyakkanavar, M. V. George, Tetrahedron 1968, 24, 1567-1575;
40. e) S. K. Khetan, M. V. George, Tetrahedron 1969, 25, 527-540;
41. f) E. Fabiano, B. T. Golding, J. Chem. Soc. Perkin Trans. 1 1991, 3371-3375;
42. g) H. Mastalerz, A. V. Gavai, B. Fink, C. Struzynski, J. Tarrant, G. D. Vite, T. W. Wong, G. Zhang, D. M. Vyas, Can. J. Chem. 2006, 84, 528-533.
43. a) O. A. Attanasi, L. De Crescentini, P. Filippone, F. Mantellini, S. Santeusanio, Arkivoc 2002, xi, 274-292;
44. b) O. A. Attanasi, L. De Crescentini, G. Favi, P. Filippone, G. Giorgi, F. Mantellini, S. Santeusanio, J. Org. Chem. 2003, 68, 1947-1953.
45. a) C. A. Kingsbury, D. Draney, A. Sopchick, W. Rissler, D. Durham, J. Org. Chem. 1976, 41, 3863-3868;
46. b) A. Padwa, D. N. Kline, J. Perumattam, Tetrahedron Lett. 1987, 28, 913-916;
47. c) A. Padwa, U. Chiacchio, D. N. Kline, J. Perumattam, J. Org. Chem. 1988, 53, 2238-2245;
48. d) T. Inokuchi, M. Okano, T. Miyamoto, J. Org. Chem. 2001, 66, 8059-8063;
49. e) M. Ferrara, B. Crescenzi, M. Donghi, E. Muraglia, E. Nizi, S. Pesci, V. Summa, C. Gardelli, Tetrahedron Lett. 2007, 48, 8379-8382;
50. f) D. P. Canterbury, A. J. Frontier, J. M. Um, P.H.-Y. Cheong, D. A. Goldfeld, R. A. Huhn, K. N. Houk, Org. Lett. 2008, 10, 4597-4600.
51. a) J. E. Dolfini, J. Org. Chem. 1965, 30, 1298-1300;
52. b) A. Ziyaei-Halimehjani, M. R. Saidi, Tetrahedron Lett. 2008, 49, 1244-1248.
53. 11N reported in this paper. These data can be obtained free of charge from The Cambridge Crystallography Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
54. a) S. Kobayashi, M. Sugiura, H. Kitagawa, W. W.-L. Lam, Chem. Rev. 2002, 102, 2227-2302;
55. b) M. Sugiura, S. Kobayashi, Angew. Chem. 2005, 117, 5306-5317;
56. Angew. Chem. Int. Ed. 2005, 44, 5176-5186.