Microwave-assisted Paal-Knorr reaction - Three-step regiocontrolled synthesis of polysubstituted furans, pyrroles and thiophenes

European Journal of Organic Chemistry

Volumn , Issue 24, 2005, Pages 5277-5288

  Minetto, Giacomo ^a   Raveglia, Luca F ^b   Sega, Alessandro ^a   Taddei, Maurizio ^a  

^a UNIVERSITY OF SIENA   (Italy)

^b NiKem Research   (Italy)

Author keywords

Cyclocondensation; Microwaves; Peptidomimetics; Pyrroles

Indexed keywords

EID: 30044440260     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200500387     Document Type: Article

References (40)

1. a) A. R. Katritzky, Chem. Rev. 2004, 104, 2125-2812.
2. For recent references on the use of heterocyclic scaffolds in CombiChem. see: b) N. Kaval, D. Ermolat'ev, P. Appukkuttan, P. W. Dehaen, C. O. Kappe, E. Van der Eycken, J. Comb. Chem. 2005, 7, 490-502;
3. c) B. Martinez-Teopel, J. Teixido, R. Pascual, M. Mora, J. Pujola, T. Fujimoto, J. I. Borell, E. L. Michelotti, J. Comb. Chem. 2005, 7, 436-448;
4. d) P. Wipf, C. R. J. Stephenson, M. A. A. Walczak, Org. Lett. 2004, 6, 3009-3012;
5. e) T. Opatz, Eur. J. Org. Chem. 2004, 4113-4118;
6. f) G. A. Strohmeier, W. Haas, C. O. Kappe, Chem. Eur. J. 2004, 10, 2919-2926;
7. g) A. Rafai Far, Angew. Chem. Int. Ed. 2003, 42, 2340-2348;
8. h) K. A. Hansford, V. Zanzarova, A. Dorr, W. D. Lubell, J. Comb. Chem. 2004, 6, 893.
9. a) S. Hirano, S. Ichikawa, A. Matsuda, Angew. Chem. Int. Ed. 2005, 44, 1854-1856;
10. b) G. Heckmann, T. Bach, Angew. Chem. Int. Ed. 2005, 44, 1199-1201;
11. c) M. Limbach, S. Dalai, A. Janssen, M. Es-Sayed, J. Magull, A. de Maijere, Eur. J. Org. Chem. 2005, 610-617.
12. A. M. Doherty, Annual Reports in Medicinal Chemistry, Elsevier, Amsterdam, 2004, vol. 39.
13. a) L. Knorr, Ber. Dtsch. Chem. Ges. 1884, 17, 1635-1642;
14. b) C. Paal, Ber. Dtsch. Chem. Ges. 1885, 18, 367-371;
15. c) A. Gossauer, Die Chemie der Pyrrole, Springer-Verlag, Berlin, 1974;
16. d) R. J. Sundberg, in Compehensive Heterocyclic Chemistry II (Eds.: A. R. Katritzky, C. W. Rees, E. F. V. Scriven), Pergamon Press, Oxford 1996, vol. 2, p. 119.
17. J. Clayden, N. Greevs, S. Warren, P. Wothers, Organic Chemistry, Oxford University Press, Oxford, 2001, p. 1188.
18. G. Minetto, L. Raveglia, M. Taddei, Org. Lett. 2004, 6, 389-392.
19. a) J. B. Brogan, C. K. Zercher, J. Org. Chem. 1997, 62, 6444-6446;
20. b) S. Lai, C. K. Zercher, J. P. Jasinski, S. N. Reid, R. J. Staples, Org. Lett. 2001, 3, 4169-4171.
21. T. Fukuyama, H. Tokuyama, Aldrichim. Acta 2004, 37, 87-96.
22. C. R. Theberge, C. K. Zercher, Tetrahedron 2003, 59, 1521-1527.
23. a) S. Jolivet-Fouchet, J. Hamelin, F. Texier-Boullet, L. Toupet, P. Jacquault, Tetrahedron 1998, 54, 4561-4578;
24. b) T. N. Danks, Tetrahedron Lett. 1999, 40, 3957-3960;
25. c) B. C. Ranu, A. Hajra, U. Jana, Synlett 2000, 75-76;
26. d) B. C. Ranu, A. Hajara, Tetrahedron 2001, 57, 4767-4773;
27. e) A. R. Bharadwaj, K. A. Scheidt, Org. Lett. 2004, 6, 2465-2468.
28. Experiments carried out with a Discover apparatus from CEM.
29. C. Betschart, L. S. Hegedus, J. Am. Chem. Soc. 1992, 114, 5010-5016.
30. For a recent review on latest developments of furan synthesis, see: R. C. D. Brown, Angew. Chem. Int. Ed. 2005, 44, 850-852.
31. An analogous reaction has been described using conventional heating: D. R. Shridhar, M. Jogibhukta, S. Rao, V. H. Handa, Synthesis 1982, 1061-1062.
32. C. Gabriel, S. Gabriel, E. H. Grant, B. S. J. Halstead, D. M. P. Mingos, Chem. Soc. Rev. 1998, 27, 213-224.
33. A. Basha, M. Lipton, S. M. Weinreb, Tetrahedron Lett. 1977, 18, 4171.
34. G. Jeannotte, W. D. Lubell, J. Am. Chem. Soc. 2004, 126, 14334-14335.
35. DMTMM: 4-(4,6-dimethoxy[1,3,5]triazin-2-yl)-4-methylmorpholinium chloride: A. Falchi, G. Giacomelli, A. Porcheddu, M. Taddei, Synlett 2000, 277.
36. M. C. Daga, M. Taddei, M. G. Varchi, Tetrahedron Lett. 2001, 42, 5191.
37. P.-K. Chiu, M. P. Sannes, Tetrahedron 1990, 46, 3439.
38. J. O. Smith, B. K. Mandal, J. Heterocycl. Chem. 1997, 34, 1441.
39. H. Stetter, F. Jonas, Chem. Ber. 1981, 114, 564.
40. H.-U. Reissig, H. Holzinger, G. Glomsda, Tetrahedron 1989, 45, 3139.