An efficient synthesis of highly substituted pyrrole and bis pyrrole derivatives

Journal of Heterocyclic Chemistry

Volumn 44, Issue 4, 2007, Pages 923-926

  Sagyam, Rajeshwar Reddy ^a   Vurimidi, Himabindu ^b   Padi, Pratap Reddy ^a   Ghanta, Mahesh Reddy ^a  

^a DR REDDY'S LABORATORIES LTD   (India)

^b JAWAHARLAL NEHRU TECHNOLOGICAL UNIVERSITY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

DIPYRROLE DERIVATIVE; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SYNTHESIS;

EID: 36749079276     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570440429     Document Type: Article

References (28)

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.
3. (c) Mach, R. H.; Huang, Y. S.; Freeman, R. A.; Wu, L.; Blair, S.; Luedtke, R. R. Bioorg. Med. Chem. 2003, 11, 225.
4. (d) Bleicher, K. H.; Wuthrich, Y.; Adam, G.; Hoffmann, T.; Sleight, A. J. Bioorg. Med. Chem. Lett. 2002, 12, 3073.
5. (e) Hackling, A. E.; Stark, H. Chem. Bio-Chem. 2002, 5, 946.
6. (f) El-Gaby, M. S. A.; Gaber, A. M.; Atalla, A. A.; Al-Wahab, K. A. A. Farmaco 2002, 57, 613.
7. (a) O'Hagan, D. Nat. Prod. Rep. 2000, 17, 435 and references therein.
8. (b) Hoffmann, H.; Lindel, T. Synthesis 2003, 1753.
9. (c) Fürstner, A. Angew. Chem., Int. Ed. 2003, 42, 3582.
10. (d) Lindquist, N.; Fenical, W.; Van Duyne, G. D.; Clardy, J. J. Org. Chem. 1988, 53, 4570.
11. (e) Boger, D.; Boyce, C. W.; Labroli, M. A.; Sehon, C. A.; Jin, Q. J. Am. Chem. Soc. 1999, 121, 54.
12. (a) Colotta, V.; Cecchi, L.; Melani, F.; Filacchioni, G.; Martini, C.; Giannaccini, G.; Lucacchini, A. J. Med. Chem. 1990, 33, 2646.
13. (b) Cozzi, P.; Mongelli, N. Curr. Pharm. Des. 1998, 4, 181.
14. (c) Huffman, J. W. Curr. Med. Chem. 1999,6, 705.
15. (a) Curran, D.; Grimshaw, J.; Perera, S. D. Chem. Soc. Rev. 1991, 20, 391.
16. (b) Deronzier, A.; Moutet, J. -C. Curr. Top. Electrochem. 1994, 3, 159.
17. (c) Lee, C. F.; Yang, L. M.; Hwu, T. Y.; Feng, A. S.; Tseng, J. C.; Luh, T. Y. J. Am. Chem. Soc. 2000, 122, 4992 and references therein.
18. (a) Knorr, L. Chem. Ber. 1884, 17, 1635.
19. (b) Paal, C. Chem. Ber. 1885, 18, 367.
20. (c) Amarnath, V.; Anthony, D. C.; Amarnath, K.; Valentine, W. M.; Wetterau, L. A.; Graham, D. G. J. Org. Chem. 1991, 56, 6924.
21. (d) Pyrroles, Part II; Jones, R. A. 1992, Wiley Ed: New York,.
22. (e) Gribble, G. W. In Comprehensive Heterocyclic Chemistry II; Katrizky, A. R.; Rees, C. W.; Scriven, E. F. Eds. Pergamon Press: Oxford, 1996; Vol. 2, p 207.
23. For a solid-phase approach to the synthesis of pyrroles from 1,4-dicarbonyl compounds, see: Raghavan, S.; Anuradha, K. Synlett 2003, 711.
24. Merlic, C. A.; Baur, A.; Aldrich, C. C. J. Am. Chem. Soc. 2000, 122, 7398.
25. Kel'in, A. V.; Sromek, A. W.; Gevorgyan, V. J. Am. Chem. Soc. 2001, 123, 2074.
26. Wang, Y. L.; Zhu, S. Z. Org. Lett. 2003, 5, 745.
27. Takaya, H.; Kojima, S.; Murahashi, S. I. Org. Utt. 2001, 3, 421.
28. Butler, D. E.; Deering, C. F.; Millar, A.; Nanninga, T. N.; Roth, B. D. WO 89/07598, 1989, Chem. Abstr. 1989, 112, 216691.