Syntheses of 2-Spiroindoles and Pyrrolo[1,2-a]indoles

Journal of Heterocyclic Chemistry

Volumn 35, Issue 2, 1998, Pages 421-428

  Malapel Andrieu, B ^a   Merour J Y ^a  

^a UNIVERSITÉ D'ORLÉANS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 1542395143     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570350227     Document Type: Article

References (29)

1. B. B. Snider and C. P. Gartaya-Marn, J. Org. Chem., 49, 1688 (1984).
2. N. Keppens and N. De Kimpe, Synlett, 285 (1994) and references therein.
3. T. Yamane and K. Ogasawara, Synlett, 925 (1996).
4. M. Fujii, K. Kawaguchi, K. Nakamura and A. Ohno, Chem. Letters, 1493 (1992).
5. M. J. Martin-Lopez and G. Bernejo, Tetrahedron Letters, 35, 4235 (1994).
6. H. E. Shoemaker and W. N. Speckamp, Tetrahedron Letters, 1515 (1978).
7. R. Stahl, R. Galli, R. Güller and H.-J. Borschberg, Helv. Chem. Acta, 77, 2125 (1994).
8. H. Takayama, Heterocycles, 42, 87 (1996).
9. J. G. Rodriguez and A. S. Andres, J. Heterocyclic Chem., 28, 1293 (1991).
10. J.-Y. Mérour, L. Chichereau, E. Desarbre and P. Gadonneix, Synthesis, 519 (1996).
11. J.-Y. Mérour, A. Mamaï, B. Malapel and P. Gadonneix, Tetrahedron, 53, 987 (1997).
12. P. C. Unangst and R. E. Brown, J. Med. Chem., 23, 1251 (1980).
13. P. C. Unangst and M. E. Carethers, J. Heterocyclic Chem., 21, 709 (1984).
14. P. C. Unangst, D. T. Connor, S. R. Stabler, R. J. Weikert, M. E. Carethers, J. A. Kennedy, D. O. Thueson, J. C. Chestnut, R. L. Adolphson and M. C. Conroy, J. Med. Chem., 32, 1360 (1989).
15. P. C. Unangst and R. E. Brown, J. Heterocyclic Chem., 21, 283 (1984).
16. P. C. Unangst, D. T. Connor and S.T. Miller, J. Heterocyclic Chem., 33, 1627 (1996).
17. D. L. Boger and T. Nishi, Bioorg. Med. Chem., 3, 67 (1995).
18. R. A. Bit, P. D. Davis, C. H. Hill, E. Keech and R. Vesey, Tetrahedron, 26, 4645 (1991).
19. M. G. Reinecke, J. F. Sebastian, H. W. Johnson Jr. and D. Puyn, J. Org. Chem., 37, 3066 (1972).
20. G. A. Epling and A. Kumar, Synlett, 347 (1991).
21. H. Plieninger, H. Sirowej and D. Rau, Chem. Ber., 104, 1863 (1971).
22. H. Plieninger and H. Herzog, Monatsh. Chem., 98, 807 (1967).
23. A. S. Bourlot and J.-Y. Mérour, Heterocyclic Commun., 1, 1781 (1995).
24. E. Houghton and J. E. Saxton, J. Chem. Soc., 595 (1959).
25. L. H. Hellberg and C. Beeson, Tetrahedron Utters, 27, 3955 (1986).
26. Compound 12 was obtained in 80% yield by reacting ethyl 3-hydroxy-1-methylindole-2-carboxylate with 3-bromopropanenitrile as for compound 8.
27. J. C. Andrade, W. F. Maier and P. V. R. Schleyer, Synthesis, 802 (1980).
28. M. Keppens and N. De Kimpe, J. Org. Chem., 60, 3916 (1995).
29. The numbering of atoms in compound 26 in Scheme 6 refer to the nmr data.