Synthesis of substituted 1,2,3,4-tetrahydro-1-thiacarbazole and spiro[pyrrolidinone-3,3′-indolinones] through a common intermediate obtained by condensation of indolin-2-one, (aryl)aldehydes, and Meldrum's acid

European Journal of Organic Chemistry

Volumn , Issue 20, 2002, Pages 3481-3490

  Cochard, Fabien ^a   Laronze, Marie ^a   Prost, Élise ^a   Nuzillard, Jean Marc ^a   Augé, Franck ^a   Petermann, Christian ^a   Sigaut, Philippe ^a   Sapi, Janos ^a   Laronze, Jean Yves ^a  

^a UNIVERSITÉ DE REIMS CHAMPAGNE ARDENNE   (France)

Author keywords

Nitrogen heterocycles; NMR spectroscopy; Peptidomimetics; Spiro compounds; Sulfur heterocycles

Indexed keywords

ALDEHYDE; AZIDE; CARBAZOLE DERIVATIVE; INDOLE DERIVATIVE; NITROGEN; OXINDOLE; SPIRO COMPOUND; SULFUR;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CONFORMATION; CYCLIZATION; NUCLEAR OVERHAUSER EFFECT; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS; ULTRAVIOLET SPECTROSCOPY;

EID: 0036774907     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200210)2002:20<3481::AID-EJOC3481>3.0.CO;2-C     Document Type: Article

References (29)

1. C. Nemes, L. Jeannin, J. Sapi, M. Laronze, H. Seghir, F. Augé, J.-Y. Laronze, Tetrahedron 2000, 56, 5479-5492.
2. F. G. Bordwell, H. E. Fried, J. Org. Chem. 1991, 56, 4218-4223.
3. [3a] N. Ishizuka, T Sato, Y. Makisumi, Chem. Pharm. Bull. 1990, 38, 1396-1399.
4. [3b] S. Takada, N. Ishizuka, T. Sasatani, Y. Makisumi, H. Jyoyama, H. Hatakeyama, F. Asanuma, K. Hirose, Chem. Pharm. Bull. 1984, 32, 877-886.
5. [3c] N. Ishizuka, M. Shiro, Y. Makisumi, J. Chem. Soc. Perkin Trans. 1 1990, 827-837.
6. [4a] M. Takasugi, N. Katsui, A. Shirata, J. Chem. Soc., Chem. Commun. 1986, 1077-1078.
7. [4b] M. Soledade, C. Pedras, F. I. Okanga, I. L. Zaharia, A. Q. Khan, Phytochemistry 2000, 53, 161-176.
8. R. G. Mehta, J. Liu, A. Constantinou, M. Hawthorne, J. M. Pezzuto, R. C. Moon, R. M. Moriarty, Anticancer Res. 1994, 14, 1209-1214.
9. A. Jossang, P. Jossang, H. A. Hadi, T. Sévenet, B. Bodo. J Org. Chem. 1991, 56, 6527-6530.
10. A. M. Thompson, M. Boyd, W. A. Denny, J. Chem. Soc., Perkin Trans. 1 1993, 1835-1837.
11. L. Sun, N. Tran, F. Tang, H. App, P. Hirth, G. McMahon, C. Tang, J. Med. Chem. 1998, 41, 2588-2603.
12. Y. Oikawa, O. Hitasawa, O. Yonemitsu, Tetrahedron Lett. 1978, 19, 1759-1762.
13. F. Cochard, J. Sapi, J.-Y. Laronze, Tetrahedron Lett. 2001, 42, 6291-6294.
14. C. Nemes, J.-Y. Laronze, Synthesis 1999, 254-257.
15. W. G. Rajeswaran, R. B. Labroo, L. A. Cohen, J. Org. Chem. 1999, 64, 1369-1371.
16. M. P. Cava, M. I. Levinson, Tetrahedron 1985, 41, 5061-5087.
17. S.-I. Bascop, J. Sapi, J.-Y. Laronze, J. Levy, Heterocycles 1994, 38, 725-732.
18. [15a] P. B. Alper, C. Meyers, A. Lerchner, D. R. Siegel, E. M. Carreira, Angew. Chem. Int. Ed., 1999, 38, 3186-3189.
19. [15b] C. Fischer, C. Meyers, E. M. Carreira, Helv. Chim. Acta 2000, 83, 1175-1181.
20. [15c] S. T. Hilton, T. C. T. Ho, G. Pljevaljcic, K. Jones, Org. Lett. 2000, 2, 2639-2641.
21. [15d] I. Fejes, M. Nyerges, A. Szöllösy, G. Blasko, L. Töke, Tetrahedron 2001, 57, 1129-1137.
22. [15e] U. K. S. Kumar, H. Ila, H. Junjappa, Org. Lett. 2001, 3, 4193-4196.
23. F. von Nussbaum, S. J. Danishefsky, Angew. Chem. Int. Ed. 2000, 39, 2175-2178.
24. V. Armstrong, O. Soto, J. A. Valderrama, R. Tapia, Synth. Commun. 1988, 18, 717-725.
25. [18a] T. A. Engler, G. A. Gfesser, B. W., Draney, J. Org. Chem. 1995, 60, 3700-3706.
26. [18b] M. Boisbrun, L. Jeannin, L. Toupet, J.-Y. Laronze, Eur. J. Org. Chem. 2000, 3051-3057.
27. D. Neuhaus, M. Williamson, The Nuclear Overhauser Effect, VCH, Weinheim, 1989, p. 103.
28. F. Mohammadi, N. G. J. Richards, W. C. Guida, R. Liskamp, M. Lipton, C. Caufield, G. Chang, T Hendrickson, W. C. Still, J. Comput. Chem. 1990, 11, 140-155.
29. Discover®, 1998 Molecular Simulations Inc., 9685 Scranton Road, San Diego, CA 92121-2777.