Zinc(II) triflate-catalyzed divergent synthesis of polyfunctionalized pyrroles

Advanced Synthesis and Catalysis

Volumn 353, Issue 4, 2011, Pages 595-605

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

^a UNIVERSITY OF URBINO   (Italy)

^b UNIVERSITY OF SIENA   (Italy)

Author keywords

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

Indexed keywords

EID: 79952560252     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201000796     Document Type: Article

References (99)

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) M. D'Ischia, A. Napolitano, A. Pezzella, in: Comprehensive Heterocyclic Chemistry III, Vol. 4, (Eds.: A. R. Katritzky, C. A. Ramsden, E. F. V. Scriven, R. J. K. Taylor), Pergamon-Elsevier Science, Amsterdam, 2008, Chapter 4;
4. d) C. Rochais, V. Lisowski, P. Dallemagne, S. Rault, Bioorg. Med. Chem. 2006, 14, 8162-8175;
5. e) R. Di Santo, R. Costi, M. Artico, G. Miele, A. Lavecchia, E. Novellino, A. Bergamini, R. Cancio, G. Maga, ChemMedChem 2006, 1, 1367-1378;
6. f) L. Zeng, E. W. Miller, A. Pralle, E. Y. Isacoff, C. J. Chang, J. Am. Chem. Soc. 2006, 128, 10-11.
7. For some examples on the use of pyrrole derivatives in material sciences see: a) L. F. Tietze, G. Kettschau, U. Heuschert, G. Normann, Chem. Eur. J. 2001, 7, 368-373;
8. b) S. S. P. Chou, Y. H. Yeh, Tetrahedron Lett. 2001, 42, 1309-1311;
9. c) G. Zotti, S. Zecchin, G. Schiavon, A, Berlin, Chem. Mater. 2002, 14, 3607-3614;
10. d) A. Naji, M. Cretin, M. Persin, J. Sarrazin, J. Membr. Sci. 2003, 212, 1-11;
11. e) 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.
12. a) H. Kikuchi, M. Sekiya, Y. Katou, K. Ueda, T. Kabeya, S. Kurata, Y. Oshima, Org. Lett. 2009, 11, 1693-1695;
13. b) R. R. Khanwelkar, G. S. Chen, H.-C. Wang, C.-W. Yu, C.-H. Huang, O. Lee, C.-H. Chen, C.-S. Hwang, C.-H. Ko, N.-T. Chou, M.-W. Lin, L.-M. Wang, Y.-C. Chen, T.-H. Hseu, C.-N. Chang, H.-C. Hsu, H.-C. Lin, Y.-C Shih, S.-H. Chou, H.-W. Tseng, C.-P. Liu, C.-M. Tu, T.-L. Hu, Y.-J. Tsai, J.-W. Chern, Bioorg. Med. Chem. 2010, 18, 4674-4686;
14. c) M. S. Mohamed, R. Kamel, S. S. Fatahala, Eur. J. Med. Chem. 2010, 45, 2994-3004.
15. a) D. G. Kaiser, E. M. Glenn, J. Pharm. Sci. 1972, 61, 1908-1911;
16. b) G. Daisone, B. Maggio, D. Schillaci, Pharmazie 1990, 45, 441-442;
17. c) A. M. Almerico, P. Diana, P. Barraja, G. Dattolo, F. Mingoia, M. Putzolu, G. Perra, C. Milia, C. Musiu, M. E. Marongiu, Farmaco 1997, 52, 667-672;
18. d) J. Lehuede, B. Fauconneau, L. Barrier, M. Ourakow, A. Piriou, J. M. Vierfond, Eur. J. Med. Chem. 1999, 34, 991-996;
19. e) G. A. Pinna, G. Loriga, G. Murineddu, G. Grella, M. Mura, L. Vargiu, C. Murgioni, P. La Colla, Chem. Pharm. Bull. 2001, 49, 1406-1411;
20. f) M. Iwao, T. Takeuchi, N. Fujikawa, T. Fukuda, F. Ishibashi, Tetrahedron Lett. 2003, 44, 4443-4446.
21. a) U. Ellervik, C. C. C. Wang, P. B. Dervan, J. Am. Chem. Soc. 2000, 122, 9354-9360;
22. b) M. A. Marques, R. M. Doss, A. R. Urbach, P. B. Dervan, Helv. Chim. Acta 2002, 85, 4485-4517;
23. c) M. A. Marques, R. M. Doss, S. Foister, P. B. Dervan, J. Am. Chem. Soc. 2004, 126, 10339-10349;
24. d) R. H. Baughman, Science 2005, 308, 63-65;
25. e) C. Baristiran, A. Erden, G. Sonmez, Polym. Prepr. Am. Chem. Soc. Div. Polym. Chem. 2006, 47, 407-408.
26. a) L. Groenendaal, E. W. Meijere, J. A. J. M. Vekemans, in: Electronic Materials: The Oligomer Approach, (Eds.: K. Müllen, G. Wegner), Wiley-VCH, Weinheim, Germany, 1997;
27. b) M. Baumgarlen, N. Tyulyulkor, Chem. Eur. J. 1998, 4, 987-989;
28. c) C.-F. Lee, L.-M. Yang, T.-Y. Hwu, A.-S. Feng, J.-C. Tseng, T.-Y. Luh, J. Am. Chem. Soc. 2000, 122, 4992-4993, and references cited therein;
29. d) R. H. Baughman, Science 2005, 308, 63-65;
30. e) C. Baristiran, A. Erden, G. Sonmez, Polym. Prepr. Am. Chem. Soc. Div. Polym. Chem. 2006, 47, 407-408.
31. a) S. Higgins, Chem. Soc. Rev. 1997, 26, 247-258;
32. b) Handbook of Conducting Polymers, (Eds.: T. A. Skotheim, R. L. Elsenbaumer, J. R. Reynolds), 2nd edn., Marcell Dekker, New York, 1998;
33. c) B. C. Thompson, K. A. Abboud, J. R. Reynolds, K. Nakatani, P. Audebert, New J. Chem. 2005, 29, 1128-1134;
34. d) P. Leiva, A. Martinez, P. Otto, Synth. Met. 2006, 156, 648-653.
35. a) J. M. Lehn, Supramolecular Chemistry; Concepts and Perceptives, VCH, Weinheim, Germany, 1995;
36. b) S. Demoustier-Champagne, J. Duchet, R. Legras, Synth. Met. 1999, 101, 20-21;
37. c) L. J. Prins, D. N. Reinhoudt, P. Timmerman, Angew. Chem. 2001, 113, 2446-2492;
38. Angew. Chem. Int. Ed. 2001, 40, 2382-2426;
39. d) W. van Zoelen, S. Bondzic, T. F. Landaluce, J. Brondijk, K. Loos, A.-J. Schouten, P. Rudolf, G. ten Brinke, Polymer 2009, 50, 3617-3625.
40. a) M. G. H. Vicente, L. Jaquinod, K. M. Smith, Chem. Commun. 1999, 1771-1782;
41. b) F. P. Montforts, O. Kutzki, Angew. Chem. 2000, 112, 612-614;
42. Angew. Chem. Int. Ed. 2000, 39, 599-601;
43. c) H. Miyaji, W. Sato, J. L. Sessler, Angew. Chem. 2000, 112, 1847-1850;
44. Angew. Chem. Int. Ed. 2000, 39, 1777-1780;
45. d) P. A. Gale, P. Anzenbacher, J. L. Sessler, Coord. Chem. Rev. 2001, 222, 57-102;
46. e) D. W. Yoon, H. Hwang, C.-H. Lee, Angew. Chem. 2002, 114, 1835-1837;
47. Angew. Chem. Int. Ed. 2002, 41, 1757-1759;
48. f) J. O. Jeppesen, J Becher, Eur. J. Org. Chem. 2003, 3245-3266.
49. a) L. Knorr, Ber. dtsch. chem. Ges. 1884, 17, 1635;
50. b) L. Knorr, H. Lange, Ber. dtsch. chem. Ges. 1902, 35, 2998.
51. For recent examples, see: 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;
52. d) C. M. Shiner, T. D. Laner, Tetrahedron 2005, 61, 11628-11640.
53. a) A. Hantzsch, Ber. dtsch. chem. Ges. 1890, 23, 1474.
54. For a recent example, see: b) V. S. Matiychuk, R. L. Martyack, N. D. Obushak, Y. V. Ostapiuk, N. I. Pidlypnyi, Chem. Heterocycl. Compd. 2004, 40, 1218-1219.
55. a) L. Knorr, Ber. dtsch. chem. Ges. 1885, 18, 299;
56. b) C. Paal, Ber. dtsch. chem. Ges. 1885, 18, 367.
57. For recent examples, see: c) G. Minetto, L. F. Raveglia, A. Sega, M. Taddei, Eur. J. Org. Chem. 2005, 5277-5288;
58. d) J. Chen, H. Wu, Z. Zheng, C. Jin, X. Zhang, W. Su, Tetrahedron Lett. 2006, 47, 5383-5387.
59. Recent examples: a) I. Nakamura, Y. Yamamoto, Chem. Rev. 2004, 104, 2127-2198;
60. b) D. J. S. Cyr, B. A. Arndtsen, J. Am. Chem. Soc. 2007, 129, 12366-12367;
61. c) S. Chiba, Y.-F. Wang, G. Lapointe, K. Narasaka, Org. Lett. 2008, 10, 313-316;
62. d) X.-T. Liu, L. Huang, F.-J. Zheng, Z.-P Zhan, Adv. Synth. Catal. 2008, 350, 2778-2788;
63. e) Y. Lu, X. Fu, H. Chen, X. Du, X. Jia, Y. Liu, Adv. Synth. Catal. 2009, 351, 129-134.
64. Recent examples: a) G. Balme, Angew. Chem. 2004, 116, 6396-6399;
65. Angew. Chem. Int. Ed. 2004, 43, 6238-6241;
66. b) D. Tejedor, D. Gonzales-Cruz, F. Garcia-Tellado, J. J. Marrero-Tellado, M. L. Rodriguez, J. Am. Chem. Soc. 2004, 126, 8390-8391;
67. c) Y. Yamamoto, H. Hayashi, T. Saigoku, H. Nishiyama, J. Am. Chem. Soc. 2005, 127, 10804-10805;
68. d) O. V. Larionov, A. de Meijere, Angew. Chem. 2005, 117, 5809-5813;
69. Angew. Chem. Int. Ed. 2005, 44, 5664-5667.
70. a) O. A. Attanasi, P. Bonifazi, E. Foresti, G. Pradella, J. Org. Chem. 1982, 47, 684-687;
71. b) O. A. Attanasi, P. Filippone, Synlett 1997, 1128-1140;
72. c) O. A. Attanasi, L. De Crescentini, G. Favi, P. Filippone, F. Mantellini, S. Santeusanio, J. Org. Chem. 2002, 67, 8178-8181;
73. d) O. A. Attanasi, L. De Crescentini, G. Favi, P. Filippone, F. Mantellini, S. Santeusanio, J. Org. Chem. 2004, 69, 2686-2692.
74. a) O. A. Attanasi, G. Favi, P. Filippone, S. Lillini, F. Mantellini, D. Spinelli, M. Stenta, Adv. Synth. Catal. 2007, 349, 907-915;
75. b) A. Schmidt, V. Karapetyan, O. A. Attanasi, G. Favi, S. Görl, F. Mantellini, P. Langer, Synlett 2007, 2965-2968;
76. 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;
77. d) O. A. Attanasi, G. Favi, P. Filippone, G. Giorgi, F. Mantellini, G. Moscatelli, D. Spinelli, Org. Lett. 2008, 10, 1983-1986.
78. O. A. Attanasi, S. Berretta, L. De Crescentini, G. Favi, G. Giorgi, F. Mantellini, Adv. Synth. Catal. 2009, 351, 715-719.
79. a) J. B. Hendrickson, R. Rees, J. Am. Chem. Soc. 1961, 83, 1250-1251;
80. b) D. S. James, P. E. Fanta, J. Org. Chem. 1962, 27, 3346-3348;
81. c) J. B. Hendrickson, R. Rees, J. F. Templeton, J. Am. Chem. Soc. 1964, 86, 107-111;
82. d) S. K. Khetan, J. G. Hiriyakkanavar, M. V. George, Tetrahedron 1968, 24, 1567-1575;
83. e) S. K. Khetan, M. V. George, Tetrahedron 1969, 25, 527-540;
84. f) E. Fabiano, B. T. Golding, J. Chem. Soc. Perkin Trans. 1 1991, 3371-3375;
85. 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.
86. a) O. A. Attanasi, L. De Crescentini, P. Filippone, F. Mantellini, S. Santeusanio, Arkivoc 2002, xi, 274-292;
87. b) O. A. Attanasi, L. De Crescentini, G. Favi, P. Filippone, G. Giorgi, F. Mantellini, S. Santeusanio, J. Org. Chem. 2003, 68, 1947-1953.
88. For the electrophilicity parameters E of DDs and the nucleophilicity parameters N of amines, see: T. Kanzian, S. Nicolini, L. De Crescentini, O. A. Attanasi, A. R. Ofial, H. Mayr, Chem. Eur. J. 2010, 16, 12008-120016, and references cited therein.
89. 11N reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC 710574. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif or on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [Fax: int. code + 44-(1223)-336-033; E-mail: deposit@ccdc.cam.ac.uk].
90. a) S. Kobayashi, M. Sugiura, H. Kitagawa, W. W.-L. Lam, Chem. Rev. 2002, 102, 2227-2302;
91. b) M. Sugiura, S. Kobayashi, Angew. Chem. 2005, 117, 5306-5317;
92. Angew. Chem. Int. Ed. 2005, 44, 5176-5186.
93. a) Y.-H. Chen, J. W. Lown, J. Am. Chem. Soc. 1994, 116, 6995-7005;
94. b) W. B. Greenberg, E. E. Baird, P. B. Dervan, Chem. Eur. J. 1998, 4, 796-805.
95. J. Hlavatý, V. Papež, L. Kavan, Synth. Met. 1994, 63, 209-212.
96. S.-B. Zhao, G.-H. Liu, D. Song, S. Wang, Dalton Trans. 2008, 48, 6953-6965.
97. CCDC 795311 contains the supplementary crystallographic data for compound 13g. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
98. a) O. A. Attanasi, P. Filippone, A. Mei, S. Santeusanio, Synthesis 1984, 671-672;
99. b) O. A. Attanasi, P. Filippone, A. Mei, S. Santeusanio, Synthesis 1984, 873-874.