Synthesis of new dehydro 2-azatryptophans and derivatives via Heck cross-coupling reactions of 3-iodoindazoles with methyl 2-(acetylamino)acrylate

Synthesis

Volumn , Issue 20, 2006, Pages 3506-3514

  Crestey, François ^a   Collot, Valérie ^a   Stiebing, Silvia ^a   Rault, Sylvain ^a  

^a CENTRE D ETUDES ET DE RECHERCHE SUR LE MÉDICAMENT DE NORMANDIE   (France)

Author keywords

2 (acetylamino) acrylate; 3 iodoindazoles; Catalytic hydrogenation; Dehydro 2 azatryptophans; Heck cross coupling reaction; Protective amino acid derivatives

Indexed keywords

ACRYLICS; AMINO ACIDS; CATALYSIS; DERIVATIVES; HYDROGENATION; SYNTHESIS (CHEMICAL);

3-IODOINDAZOLES; ACRYLATES; CATALYTIC HYDROGENATION; CROSS COUPLING REACTIONS;

NITROGEN COMPOUNDS;

2 ACETYLAMINO 3 [1 [2 (TRIMETHYLSILANYL)ETHOXYMETHYL] 1H INDAZOL 3 YL]PROPANOIC ACID METHYL ESTER; 2 AZATRYPTOPHAN DERIVATIVE; 3 IODO 1 [2 (TRIMETHYLSILANYL)ETHOXYMETHYL] 1H INDAZOLE; 3 IODO 1H INDAZOLE; 3 IODO 5 METHOXY 1 [2 (TRIMETHYLSILANYL)ETHOXYMETHYL] 1H INDAZOLE; 3 IODO 5 METHOXY 1H INDAZOLE; 3 IODO 5 NITRO 1 [2 (TRIMETHYLSILANYL)ETHOXYMETHYL] 1H INDAZOLE; 3 IODO 5 NITRO 1H INDAZOLE; 3 IODOINDAZOLE DERIVATIVE; 3,5 DIIODO 1 [2 (TRIMETHYLSILANYL)ETHOXYMETHYL] 1H INDAZOLE; 3,5 DIIODO 1H INDAZOLE; 5 BENZYLOXY 3 IODO 6 METHYL 1 [2 (TRIMETHYLSILANYL)ETHOXYMETHYL] 1H INDAZOLE; 5 BENZYLOXY 3 IODO 6 METHYL 1H INDAZOLE; 5 BENZYLOXY 6 METHYL 1H INDAZOLE; 5 BROMO 1H INDAZOLE; 5 BROMO 3 IODO 1 [2 (TRIMETHYLSILANYL)ETHOXYMETHYL] 1H INDAZOLE; 5 BROMO 3 IODO 1H INDAZOLE; 5 IODO 1H INDAZOLE; 5 METHOXY 1H INDAZOLE; ACRYLIC ACID DERIVATIVE; AMINO ACID DERIVATIVE; INDAZOLE DERIVATIVE; METHYL 2 (ACETYLAMINO)ACRYLIC ACID; TRYPTOPHAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CROSS COUPLING REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; HECK REACTION; HYDROGENATION;

EID: 33750581638     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-950242     Document Type: Article

References (41)

1. (a) Elderfield, R. C. In Heterocyclic Compounds, Vol. 5; Elderfield, R. C., Ed.; John Wiley and Sons, Inc.: New York, 1957, 162.
2. (b) Behr, L. C.; Fusco, R.; Jacobe, C. H. In Pyrazoles, Pyrazolines, Pyrazolidines, Indazoles and Condensed Rings; Wiley, R. H., Ed.; International Wiley Science: New York, 1969, 289.
3. (c) Elguero, J. In Comprehensive Heterocyclic Chemistry, Vol 5; Katritzky, A. R.; Rees, C. W., Eds.; Pergamon Press: New York, 1984, 167.
4. Villa, R.; Orlandi, L.; Berruti, A.; Dogliotti, L.; Zaffaroni, N. Int. J. Oncol. 1999, 14, 133.
5. Palazzo, G.; Corsi, G.; Baiocchi, L.; Silvestrini, B. J. Med. Chem. 1966, 9, 38.
6. Sanger, G. J.; Nelson, D. R. Eur. J. Pharmacol. 1989, 159, 113.
7. Wu, C. C.; Ko, F. N.; Kuo, S. C.; Lee, F. Y.; Teng, C. M. Br. J. Pharmacol. 1995, 116, 1973.
8. Moore, P. K.; Wallace, P.; Gaffen, Z.; Hart, S. L.; Babbedge, R. C. Br. J. Pharmacol. 1993, 110, 219.
9. Foloppe, N.; Fisher, L. M.; Francis, G.; Howes, R.; Kierstan, P.; Potter, A. Bioorg. Med. Chem. 2006, 14, 1792.
10. McBride, C. M.; Renhowe, P. A.; Heise, C.; Jansen, J. M.; Lapointe, G.; Ma, S.; Piñeda, R.; Vora, J.; Wiesmann, M.; Shafer, C. M. Bioorg. Med. Chem Lett. 2006, 16, 3595.
11. (a) Arnautu, A.; Collot, V.; Calvo Ros, J.; Alayrac, C.; Witulski, B.; Rault, S. Tetrahedron Lett. 2002, 43, 2695.
12. (b) Collot, V.; Varlet, D.; Rault, S. Tetrahedron Lett. 2000, 41, 4363.
13. (a) Collot, V.; Dallemagne, P.; Bovy, P. R.; Rault, S. Tetrahedron 1999, 55, 6917.
14. (b) Collot, V.; Bovy, P. R.; Rault, S. Tetrahedron Lett. 2000, 47, 9053.
15. (c) Witulski, B.; Azcon, J. R.; Alayrac, C.; Arnautu, A.; Collot, V.; Rault, S. Synthesis 2005, 771.
16. Crestey, F.; Collot, V.; Stiebing, S.; Rault, S. Tetrahedron 2006, 62, 7772.
17. (a) Heck, R. F. In Comprehensive Organic Synthesis, Vol. 4; Trost, B. M., Ed.; Pergamon: New York, 1991, Chap. 4.3.
18. (b) de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379.
19. (c) Cutolo, M.; Fiandanese, V.; Naso, F.; Sciacovelli, O. Tetrahedron. Lett. 1983, 24, 4603.
20. (d) Fournier Dit Chabert, J.; Gozzi, C.; Lemaire, M. Tetrahedron. Lett. 2002, 43, 1829.
21. (e) Xin, Z.; Oost, T. K.; Abad-Zapatero, C.; Hajduk, P. J.; Pei, Z.; Szczepankiewicz, B. G.; Hutchins, C. W.; Ballaron, S. J.; Stashko, M. A.; Lubben, T.; Trevillyan, J. M.; Jirousek, M. R.; Liu, G. Bioorg. Med Chem. Lett. 2003, 13, 1887.
22. (f) Briot, A.; Baehr, C.; Brouillard, R.; Wagner, A.; Mioskowski, C. J. Org. Chem. 2004, 69, 1374.
23. (a) Harrington, P. J.; Hegedus, L. S. J. Org. Chem. 1984, 49, 2657.
24. (b) Harrington, P. J.; Hegedus, L. S.; McDaniel, K. F. J. Am. Chem. Soc. 1987, 109, 4335.
25. (c) Gallou-Dagommer, I.; Gastaud, P.; RajanBabu, T. V. Org. Lett. 2001, 3, 2053.
26. (d) Bozell, J. J.; Vogt, C. E.; Gozum, J. J. Org. Chem. 1991, 56, 2584.
27. (e) Carlström, A.-S.; Frejd, T. Synthesis 1989, 414.
28. (f) Basu, B.; Chattopadhyay, S. K.; Ritzen, A.; Frejd, T. Tetrahedron: Asymmetry 1997, 8, 1841.
29. (g) Ritzen, A.; Basu, B.; Chattopadhyay, S. K.; Dossa, F.; Frejd, T. Tetrahedron: Asymmetry 1998, 9, 503.
30. (h) Jeffery, T. J. Chem. Soc., Chem. Commun. 1984, 1287.
31. (i) Jeffery, T. Tetrahedron Lett. 1985, 26, 2667.
32. (a) Kania, R. S.; Bender, S. L.; Borchardt, A. J.; Braganza, J. F.; Cripps, S. J.; Hua, Y.; Johnson, M. D.; Johnson, T. O. Jr.; Luu, H. T.; Palmer, C. L.; Reich, S. H.; Tempczyk-Russell, A. M.; Teng, M.; Thomas, C.; Varney, M. D.; Wallace, M. B. WO 0102369 A2, 2001; Chem. Abstr. 2001, 134, 100864.
33. (b) Reich, S. H.; Bleckman, T. M.; Kephart, S. E.; Romines, W. H. III; Wallace, M. B. WO 0153268 A2, 2001; Chem. Abstr. 2001, 135, 137505.
34. (a) Schumann, P.; Collot, V.; Hommet, Y.; Gsell, W.; Dauphin, F.; Sopkova, J.; McKenzie, E. T.; Duval, D.; Boulouard, M.; Rault, S. Bioorg. Med. Chem. Lett. 2001, 11, 1153.
35. (b) Bartsch, R.-A.; Yang, I.-W. J. Heterocycl. Chem. 1984, 21, 1063.
36. Luo, G.; Chen, L.; Dubowchik, G. J. Org. Chem. 2006, 71, 5392.
37. (a) Shimohigashi, Y.; Nitz, T. J.; Stammer, C. H.; Unubushi, T. Tetrahedron Lett. 1982, 23, 3235.
38. (b) Crombie, A. L.; Kane, J. L. Jr.; Shea, K. M.; Danheiser, R. L. J. Org. Chem. 2004, 69, 8652.
39. (a) Rousseau, J.-F.; Dodd, R. H. J. Org. Chem. 1998, 63, 2731.
40. (b) Beecher, J. E.; Tirrell, D. A. Tetrahedron Lett. 1998, 39, 3927.
41. Adams, L. A.; Aggarwal, V. K.; Bonnert, R. V.; Bressel, B.; Cox, R. J.; Shepherd, J.; de Vicente, J.; Walter, M.; Whittingham, W. G.; Winn, C. L. J. Org. Chem. 2003, 68, 9433.