Alkoxycarbonylcarbene transfer to semicyclic enaminones - A route to cyclopenta[b]pyrrole and indole ring systems

European Journal of Organic Chemistry

Volumn , Issue 6, 1998, Pages 1177-1187

  Müller, Andreas ^a   Maier, Alexandra ^a   Neumann, Ralf ^a   Maas, Gerhard ^a  

^a UNIVERSITY OF ULM   (Germany)

Author keywords

Carbenes; Diazo compounds; Enaminones; Heterocycles; Indoles

Indexed keywords

EID: 0348082239     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1099-0690(199806)1998:6<1177::aid-ejoc1177>3.0.co;2-0     Document Type: Article

References (29)

1. M. Regitz (Ed.), Methoden Org. Chem. (Houben-Weyl), vol. E19b ["Carbene(oide), Carbine"], Thieme, Stuttgart, 1989.
2. [2a] M. P. Doyle in Comprehensive Organometallic Chemistry II, vol. 12 (Ed.: L. S. Hegedus), Elsevier, Oxford, 1995, chapters 5.1 and 5.2.
3. [2b] T. Ye, M. A. McKervey, Chem. Rev. 1994, 94, 1091-1160.
4. [2c] H. M. L. Davies in Comprehensive Organic Synthesis; Selectivity, Strategy and Efficiency in Modern Organic Chemistry, vol. 4 (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991, chapter 4.8.
5. M. N. Eberlin, C. Kascheres, J. Org. Chem. 1988, 53, 2084-2086.
6. R. Augusti, M. N. Eberlin, C. Kascheres, J. Heterocycl Chem. 1995, 32, 1355-1357.
7. G. Maas, A. Müller, J. Prakt. Chem. 1998, 340, 315-322.
8. V. Virmani, M. B. Nigam, P. C. Jaim, N. Anand, Indian J. Chem., Sect. B 1979, 17, 472-477.
9. N. Anand, J. Singh, Tetrahedron 1988, 44, 5975-5999.
10. 4 followed by addition of NaOEt has been described: C. Herdeis, A. Dimmerling, Arch. Pharm. (Weinheim) 1986, 319, 473-475.
11. G. W. Gribble in Comprehensive Heterocyclic Chemistry II (Eds.: A. R. Katritzky, C. W. Rees, E. F. V. Scriven), vol. 2 (Ed.: C. W. Bird), Elsevier, Oxford, 1996, chapter 2.04.
12. [10a] R. A. Jones, M. T. P. Marriott, W. P. Rosenthal, J. S. Arques, J. Org. Chem. 1980, 45, 4515-4519.
13. [10b] M. Murase, S. Yoshida, T. Hosaka, S. Tobinaga, Chem. Pharm. Bull. 1991, 39, 489-492.
14. L. M. Hodges, M. L. Spera, M. W. Moody, W. D. Herman, J. Am. Chem. Soc. 1996, 118, 7117-7127.
15. [12a] W. E. Noland, K. J. Kim, C. K. Lee, S. K. Bae, C. S. Hahn, J. Org. Chem. 1980, 45, 4582-4584.
16. [12b] W. E. Noland, C. K. Lee, S. K. Bae, B. Y. Chung, C. S. Hahn, K. J. Kim, J. Org. Chem. 1983, 48, 2488-2491.
17. P. Ahuja, J. Singh, N. Anand, Indian J. Chem., Sect. B 1982, 21, 142-143.
18. The easy ring opening of vicinally donor-acceptor-substituted cyclopropanes is well documented: E. Vilsmaier in The Chemistry of the Cyclopropyl Group (Ed.: Z. Rappoport), Wiley, Chichester, 1987, chapter 22; H.-U. Reißig, Top. Curr. Chem. 1988, 144, 73-135.
19. The easy ring opening of vicinally donor-acceptor-substituted cyclopropanes is well documented: E. Vilsmaier in The Chemistry of the Cyclopropyl Group (Ed.: Z. Rappoport), Wiley, Chichester, 1987, chapter 22; H.-U. Reißig, Top. Curr. Chem. 1988, 144, 73-135.
20. A. I. Meyers, A. H. Reine, J. C. Sicar, K. B. Rao, S. Singh, H. Weidmann, M. Fitzpatrick, J. Heterocycl. Chem. 1968, 5, 151-159.
21. G. Maas, R. Reinhard, R. Neumann, M. Glaser, J. Prakt. Chem. 1996, 338, 441-450.
22. [17a] N. E. Searle, Org. Synth. Coll. Vol. IV, 1963, 424-426.
23. [17b] H.-U. Reissig, J. Reichelt, T. Kunz, Org. Synth. 1992, 71, 189-199.
24. M. Regitz, J. Hocker, A. Liedhegener, Org. Synth. Coll. Vol. V, 1973, 179-183.
25. .[19b].
26. [19a] M. M. Gugelchuk, D. J. Hart, Y.-M. Tsai, J. Org. Chem. 1981, 46, 3671-3675.
27. [19b] A. S. Howard, G. C. Gerrans, J. P. Michael, J. Org. Chem. 1980, 45, 1713-1715.
28. M. Yamaguchi, I. Hirao, J. Org. Chem. 1985, 50, 1975-1977.
29. Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-101090. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [Fax: int. code + 44(1223)336-033; E-mail: deposit@ccdc.cam.ac.uk].