Tandem radical addition/cyclization of 1-(2-iodoethyl)indoles and pyrroles with methyl acrylate under Fenton-type conditions

Arkivoc

Volumn 2002, Issue 12, 2002, Pages 15-22

  Miranda, Luis D ^a   Cruz Almanza, Raymundo ^a   Pavón, Miriam ^a  

^a UNIVERSIDAD NACIONAL AUTÓNOMA DE MÉXICO   (Mexico)

Author keywords

Benzindolizidine; Fenton type oxidation; Free radicals; Indolizidine; Radical addition

Indexed keywords

1 (2 IODOETHYL) 1H PYRROLE 2 CARBALDEHYDE; 1 (2 IODOETHYL) 1H PYRROLE 3 CARBALDEHYDE; 3 FORMYL 1 (2 IODOETHYL)INDOLE; ACRYLIC ACID METHYL ESTER; CARBOXYLIC ACID DERIVATIVE; DIMETHYL 6,7,8,9 TETRAHYDROPYRIDO[1,2 A]INDOLE 9,10 DICARBOXYLATE; INDOLE DERIVATIVE; INDOLIZINE DERIVATIVE; METHYL 1 FORMYL 5,6,7,8 TETRAHYDROINDOLIZINE 8 CARBOXYLATE; METHYL 10 CYANO 6,7,8,9 TETRAHYDROPYRIDO[1,2 A]INDOLE 9 CARBOXYLATE; METHYL 10 ETHOXY(OXO)ACETYL 6,7,8,9 TETRAHYDROPYRIDO[1,2 A]INDOLE 9 CARBOXYLATE; METHYL 10 FORMYL 6,7,8,9 TETRAHYDROPYRIDO[1,2 A]INDOLE 9 CARBOXYLATE; METHYL 3 FORMYL 5,6,7,8 TETRAHYDROINDOLIZINE 8 CARBOXYLATE; METHYL 6,7,8,9 TETRAHYDROPYRIDO[1,2 A]INDOLE 9 CARBOXYLATE; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; FENTON REACTION; RADICAL REACTION; SYNTHESIS;

EID: 3242698598     PISSN: 14246376     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (39)

1. (a) Murphy, J. A.; Sherburn, M. S. Tetrahedron 1991, 47, 4077.
2. (b) Suzuki, F.; Kuroda, K. J. Heterocyclic Chem. 1993, 30, 811.
3. (c) Antonio, Y.; De la Cruz, E.; Galeazzi, E.; Guzman, A.; Bray, B. L.; Greenhuouse, R.; Kurz, L. J.; Lustig, D. A.; Maddox, M. L.; Muchowski, J. M. Can. J. Chem. 1994, 72, 15.
4. (d) Axon, J.; Boiteau, L.; Boivin, J.; Forbes, J. E.; Zard, S. Z. Tetrahedron Lett., 1994, 35, 1719.
5. (e) Tim, C. T.; Jones, K.; Wilkinson, J. Tetrahedron Lett. 1995, 36, 6743.
6. (f) Osaki, S.; Mitoh, H.; Ohmori, H. Chem. Pharm. Bull. 1996, 44, 2020.
7. (g) Dobbs, P. A.; Jones, K.; Veal, K. T. Tetrahedron 1997, 53, 8287.
8. (h) Aldabbagh, F.; Bowman, W. R.; Mann, E. Tetrahedron Lett. 1997, 38, 7937.
9. (i) Ziegler, F. E.; Belema, M. J. Org. Chem. 1997, 62, 1083.
10. (j)) Moody, C. J.; Norton, C. L. J. Chem. Soc., Perkin Trans. 1, 1997, 2639.
11. (k) Liard, A.; Quiclet-Sire, B.; Saicic, R. N.; Zard, S. Z. Tetrahedron Lett. 1997, 38, 1759.
12. (l) Liard, A.; Quiclet-Sire, B.; Saicic, R. N.; Zard, S. Z. Tetrahedron Lett. 1997, 38, 1759.
13. (m) Cholleton, N.; Zard, S. Z. Tetrahedron Lett. 1998, 39, 7295.
14. (n) Harrowen, D.; Nunn, M. I. T. Tetrahedron Lett. 1998, 39, 5875.
15. (o) Aldabbagh, F.; Bowman, W. R.; Mann, E.; Slawin, A. M. Z. Tetrahedron 1999, 55, 8111.
16. (p) Ly, T.-M.; Quiclet-Sire, B.; Sortais, B.; Zard, S. Z. Tetrahedron Lett. 1999, 40, 2533.
17. (q) Kaoudi, T.; Quiclet-Sire, B.; Seguin, S.; Zard, S. Z. Angew. Chem. Int. Ed. 2000, 39, 732.
18. (r) Marco-Contelles, J.; Rodríquez-Fernández, M. Tetrahedron Lett. 2000, 41, 381.
19. (s) Bowman, W. R.; Mann, E.; J. Chem. Soc. Perkin Trans. 1, 2000, 2991.
20. Miranda, L. D.; Cruz-Almanza, R.; Pavon, M.; Romero, Y.; Muchowski, J. M. Tetrahedron Lett. 2000, 41, 10181.
21. (a) Bennasar, M.-Ll.; Roca, T.; Griera, R.; Bosch, J. J. Org. Chem. 2001, 66, 7547.
22. (b) Bennasar, M.-Ll.; Roca, T.; Griera, R.; Bosch, J. J. Org. Chem. 2002, 67, 5537.
23. Muchowski, J. M.; Cho, I. S.; Jaime-Figueroa, S.; Artis, R. D. J. Org. Chem. 1994, 59, 2456.
24. (a) Bertilsson, B-M.; Gustafsson, B.; Kuhn, I.; Torssell, K. Acta Chem. Scand. 1970, 24, 3590.
25. (b) Rudquist, U; Torssell, K, ibid. 1971, 25, 2183.
26. (c) Torssell, K. Angew. Chem. Int. Ed. Engl. 1972, 11, 241.
27. (d) Dixon, W. T.; Norma, R. O. C.; Buley, A. L. J. Chem. Soc. 1964, 3625.
28. (e) Veltwisch, D.; Janata, E.; Asmus, K-D. J. Chem. Soc. Perkin Trans. 2, 1980, 146.
29. Minisci, F.; Vismara, E.; Fontana, F. J. Org. Chem. 1989, 54, 5224.
30. (a) Bacciochi, E.; Muraglia, E.; Sleiter, G. J. Org. Chem. 1992, 57, 6817,
31. (b) Bacciochi, E.; Muraglia, E.; Sleiter, G. Tetrahedron Lett. 1993, 34, 3799.
32. Starting materials were prepared as reported before: Miranda, L. D.; Cruz-Almanza, R.; Pavón, M.; Alva, E.; Muchowski, J. M. Tetrahedron Lett.1999, 40, 7153.
33. Branson Models B-2200R-B ultrasonic bath type cleaners were used.
34. For reviews on Indolizidine alkaloids, see: (a) Talcahata, H.; Momose, T. In The Alkaloids; Cordell, G. A. Ed.; Academic Press: San Diego, 1993, Vol. 44, Chapter 3, p.189.
35. (b) Wrobel, J. T. In The Alcaloids: Chemistry and Pharmacology; Brossi, A., Ed.; Academic Press: San Diego, 1985; Vol. 26, Chapter 7, p. 327, and references cited therein.
36. For a recent report on an acyl radical addition in a similar system at 2-C position see: Allin, S. M.; Barton, W. R. S.; Bowman, W. R.; McInally, T. Tetrahedron Lett. 2001, 42, 7887.
37. Gonzalez, C.; Greenhouse, R.; Tallabs, R.; Muchowski, J. M. Can. J. Chem.1983, 61, 1697.
38. Bray, B. L.; Mathies, P. H.; Naef, R.; Solas, D. R.; Tidwell, T. T.; Artis, D. R.; Muchowski, J. M. J. Org. Chem. 1990, 55, 6317.
39. Wong, M.W.; Pross, A.; Radom, L. J. Am. Chem. Soc. 1993, 115, 11050.