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

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