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DOI: 10.1039/A704217E (Paper) Reference Section for: Chem. Commun., 1997, 1873-1874

One-step syntheses of the pyrrolo[3,4-b]indole and pyrrolo[2,3-b]indole ring systems from 3-nitroindoles

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Erin T. Pelkey

Abstract

The reaction of 1-ethoxycarbonyl-3-nitroindole with ethyl isocyanoacetate in the presence of DBU gives ethyl 4-ethoxycarbonyl-2,4-dihydropyrrolo[3,4-b]indole-3-carboxylate, averting a novel rearrangement that we previously reported with 3-nitro-1-phenylsulfonylindole that yielded ethyl 8-phenylsulfonyl-1,8-dihydropyrrolo[2,3-b]indole-2-carboxylate.

References

  1. E. T. Pelkey, L. Chang and G. W. Gribble, Chem. Commun., 1996, 1909 RSC.
  2. G. D. Hartmann and L. M. Weinstock, Org. Synth., 1988, Coll. Vol. VI, 620.
  3. D. H. R. Barton and S. Z. Zard, J. Chem. Soc., Chem. Commun., 1985, 1098 RSC; D. H. R. Barton, J. Kervagoret and S. Z. Zard, Tetrahedron, 1990, 46, 7587 CrossRef CAS.
  4. W. M. Welch, J. Org. Chem., 1976, 41, 2031 CrossRef CAS.
  5. C.-K. Sha, K.-S. Chuang and J.-J. Young, J. Chem. Soc., Chem. Commun., 1984, 552 Search PubMed; C.-K. Sha, K.-S. Chuang and S.-J. Wey, J. Chem. Soc., Perkin Trans. 1, 1987, 977 RSC; C.-K. Sha and J.-F. Yang, Tetrahedron, 1992, 48, 10 645 CrossRef CAS.
  6. R. P. Kreher and G. Dyker, Z. Naturforsch. Teil B: Chem. Sci., 1987, 42, 473 CAS; G. Dyker and R. P. Kreher, Chem.-Ztg., 1988, 112, 235 Search PubMed.
  7. A. Jeevendam and P. C. Srinivasan, J. Chem. Soc., Perkin Trans. 1, 1995, 2663 RSC.
  8. U. Pindur and H. Erfanian-Abdoust, Chem. Rev., 1989, 89, 1681 CrossRef CAS.
  9. M. G. Saulnier and G. W. Gribble, Tetrahedron Lett., 1983, 24, 5435 CrossRef CAS; G. W. Gribble, M. G. Saulnier, M. P. Sibi and J. A. Obaza-Nutaitis, J. Org. Chem., 1984, 49, 4518 CrossRef CAS; D. A. Davis and G. W. Gribble, Tetrahedron Lett., 1990, 31, 1081 CrossRef CAS; G. W. Gribble, Adv. Heterocycl. Nat. Prod. Synth., 1990, 1, 43 Search PubMed; G. W. Gribble, Synlett, 1991, 289 CrossRef CAS; G. W. Gribble, D. J. Keavy, D. A. Davis, M. G. Saulnier, B. Pelcman, T. C. Barden, M. P. Sibi, E. R. Olson and J. J. BelBruno, J. Org. Chem., 1992, 57, 5878 CrossRef CAS.
  10. F. G. Bordwell, Acc. Chem. Res., 1988, 21, 456 CrossRef CAS and references cited therein.
  11. G. Berti, A. D. Settimo and E. Nannipieri, J. Chem. Soc. C, 1968, 2145 RSC.
  12. E. Wenkert, P. D. R. Moeller and S. R. Piettre, J. Am. Chem. Soc., 1988, 110, 7188 CrossRef CAS.
  13. K. Seki, K. Ohkura, M. Terashima and Y. Kanaoka, Heterocycles, 1994, 37, 993 CrossRef CAS.
  14. D. Dhanak and C. B. Reese, J. Chem. Soc., Perkin Trans. 1, 1986, 2181 RSC.
  15. T. Itahara, Synthesis, 1979, 151 CrossRef CAS.
  16. C. J. Moody and J. G. Ward, J. Chem. Soc., Perkin Trans. 1, 1984, 2903 RSC.
  17. A. M. van Leusen, H. Siderius, B. E. Hoogenboom and D. van Leusen, Tetrahedron Lett., 1972, 13, 5337 CrossRef.
  18. G. W. Gribble, T. C. Barden and D. A. Johnson, Tetrahedron, 1988, 44, 3195 CrossRef CAS.