Synthesis and reactivity of (3-oxo-2,3-dihydro-1H-indol-2-ylidene)acetic acid alkyl esters in Diels-Alder reactions

Synthesis

Volumn , Issue 4, 1996, Pages 519-524

  Mérour, Jean Yves ^a   Chichereau, Lucien ^a   Desarbre, Eric ^a   Gadonneix, Philippe ^a  

^a UNIVERSITÉ D'ORLÉANS   (France)

Author keywords

1H indol 3(2H) one; aldolisation; Diels Alder reactions; glyoxal derivatives; pyrrolo 2,3 b pyridin 3 on e

Indexed keywords

INDOLE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; INFRARED SPECTROPHOTOMETRY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029867934     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-4236     Document Type: Article

References (30)

1. Boger, D. L. In Comprehensive Organic Synthesis, Vol. 5; Trost, B. M. Ed.; Pergamon: New York, 1991; p 451.
2. Lambert, J. D.; Porter, Q. N. Aust. J. Chem. 1981, 34, 1483.
3. Pindur, U.; Rogge, M.; Rehn, M.; Massa, W.; Peschel, B. J. Heterocycl. Chem. 1994, 31, 981 and references therein.
4. Pindur, U. Heterocycles 1988, 27, 1253.
5. Dufour, B.; Motorina, I.; Fowler, F. W.; Grierson, D. S. Heterocycles 1994, 37, 1455. Blechert, S.; Knier, R.; Schroers, H.; Wirth, T. Synthesis 1995, 592.
6. Dufour, B.; Motorina, I.; Fowler, F. W.; Grierson, D. S. Heterocycles 1994, 37, 1455. Blechert, S.; Knier, R.; Schroers, H.; Wirth, T. Synthesis 1995, 592.
7. Kuehne, M. E.; Roland, D. M.; Hafter, R. J. Org. Chem. 1978, 43, 3705.
8. Lévy, J.; Sapi, J.; Laronze, J-Y.; Royer, D.; Toupet, L. Synlett 1992, 601.
9. Bäckvall, J-E.; Plobeck, N. A.; Juntunen, S. K. Tetrahedron Lett. 1989, 30, 2589.
10. Padwa, A.; Gareau, Y.; Harrison, B.; Rodriguez, A. J. Org. Chem. 1992, 57, 3540.
11. Wenkert, E.; Moeller, P. D. R.; Piettre, E. R. J. Am. Chem. Soc. 1988, 110, 7188.
12. Kraus, G. A.; Bougie, D.; Jacobsen, R. A.; Su, Y. J. Org. Chem. 1989, 54, 2425.
13. Wenkert, E.; Liu, S. Synthesis 1992, 323.
14. Stahl, R.; Galli, R.; Güller, R.; Borschberg, H-J. Helv. Chim. Acta 1994, 77, 2125.
15. Sanz-Cervera, J. F.; Glinka, T.; Williams, R.M. Tetrahedron 1993, 49, 8471.
16. Wu, E. S. C.; Kover, A. Synth. Commun. 1994, 24, 273.
17. Chorvat, R. J. J. Org. Chem. 1978, 43, 3778. Fontenla, J. A.; Osuna, J.; Rosa, E.; Castro, M. E.; G-Ferreiro, T.; Loza-Garcia, I.; Calleja, J. M.; Sanz, F.; Rodríguez, J.; Raviña, E.; Fueyo, J.; F-Masaguer, C.; Vidal, A.; de Ceballos, M. L. J. Med. Chem. 1994, 37, 2564.
18. Chorvat, R. J. J. Org. Chem. 1978, 43, 3778. Fontenla, J. A.; Osuna, J.; Rosa, E.; Castro, M. E.; G-Ferreiro, T.; Loza-Garcia, I.; Calleja, J. M.; Sanz, F.; Rodríguez, J.; Raviña, E.; Fueyo, J.; F-Masaguer, C.; Vidal, A.; de Ceballos, M. L. J. Med. Chem. 1994, 37, 2564.
19. Pettit, G. R.; Green, B.; Dunn, G. L. J. Org. Chem. 1970, 35, 1367.
20. Kometani, T.; Shiotani, S.; Mitsuhashi, K. Chem. Pharm. Bull. 1976, 24, 541.
21. Shen, W.; Coburn, C. A.; Bornmann, W. G.; Danishefsky, S. J. J. Org. Chem. 1993, 58, 611.
22. Paulvannan, K.; Stille, J. R. J. Org. Chem. 1994, 59, 1613.
23. Buzas, A.; Mérour, J-Y. Synthesis 1989, 458.
24. Mérour, J-Y.; Mérour, A. Synthesis 1994, 767.
25. Mérour J-Y. unpublished results.
26. Stahl, R.; Borschberg, H-J. Helv. Chim. Acta 1994, 77, 1331.
27. Güller, R.; Borschberg, H-J. Tetrahedron Lett. 1994, 35, 865.
28. Mérour, J-Y.; Piroëlle, S.; Cossais, F. Heterocycles 1993, 36, 1287.
29. Mahboobi, S.; Bernauer, K. Helv. Chim. Acta 1988, 71, 2034.
30. Desarbre, E.; Mérour, J-Y. Tetrahedron Lett. 1994, 35, 1995.