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DOI: 10.1039/A809321K (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 1, 1999, 421-426

ν-Triazolines. Part 41.1 A new synthesis of 2-alkylquinazolines and 2,9-dialkylpyrimido[4,5-b]indoles

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Emanuela Erba, Donato Pocar and Marinella Valle

Abstract

2-Alkylquinazolines were obtained from amidines by reaction with ammonia. The synthesis has been applied to the preparation of 2,9-dialkylpyrimido[4,5-b]indoles, in a one pot reaction, from 1-alkyl-2-azidoindole-3-carbaldehydes, a secondary amine and aldehydes and reaction with ammonia.

References

  1. Part 40. E. Erba, D. Pocar and P. Trimarco, J. Chem. Soc., Perkin Trans. 1, 1998, 3535 Search PubMed.
  2. M. Battistini, E. Erba and D. Pocar, J. Chem. Soc., Perkin Trans. 1, 1993, 339 RSC; Synthesis, 1992, 1206 Search PubMed.
  3. E. M. Beccalli, E. Erba, M. L. Gelmi and D. Pocar, J. Chem. Soc., Perkin Trans. 1, 1996, 1359 RSC.
  4. R. Angelini, E. Erba and D. Pocar, J. Chem. Soc., Perkin Trans. 1, 1996, 837 RSC.
  5. E. Erba, G. Mai and D. Pocar, J. Chem. Soc., Perkin Trans. 1, 1992, 1709 RSC.
  6. E. Erba and D. Sporchia, J. Chem. Soc., Perkin Trans. 1, 1997, 3021 RSC.
  7. P. Kadaba, B. Stanovnik and M. Ti[s with combining breve]ler, Adv. Heterocycl. Chem., 1984, 37, 329 and references cited therein.
  8. M. C. Koshy, D. Mickley, J. Bourgoignie and M. D. Blaufox, Circulation, 1977, 55, 533 Search PubMed; K. Unde and T. Benneche, Comprehensive Heterocyclic Chemistry II, eds. A. R. Katritzky, C. W. Rees and E. F. V. Scriven, Pergamon, Oxford, 1996, vol. 6, p. 227 Search PubMed.
  9. S. Klutchko and M. Von Strandmann, US 3 847 920 (Chem. Abstr., 1975, 82, 57722j) Search PubMed; C. E. Muller, U. Geis, B. Grahner, W. Lanzner and K. Eger, J. Med. Chem., 1996, 39, 2482 Search PubMed.
  10. A. Corsini, personal communication.
  11. K. Unde and T. Benneche, Comprehensive Heterocyclic Chemistry II, eds. A. R. Katritzky, C. W. Rees and E. F. V. Scriven, Pergamon, Oxford, 1996, vol. 6, p. 208 Search PubMed.
  12. P. Knowles, Comprehensive Heterocyclic Chemistry II, eds. A. R. Katritzky, C. W. Rees and E. F. V. Scriven, Pergamon, Oxford, 1996, vol. 7, p. 498 Search PubMed.
  13. D. Pocar, R. Stradi and L. M. Rossi, J. Chem. Soc., Perkin Trans. 1, 1972, 619 RSC.
  14. D. Pocar, E. Roversi, P. Trimarco and G. Valgattarri, Liebigs Ann. Chem., 1995, 487 Search PubMed.
  15. R. Fusco, G. Bianchetti and D. Pocar, Gazz. Chim. Ital., 1961, 91, 933 CAS.
  16. D. L. Coffen, R. I. Fryer, D. A. Katonat and F. Wong, J. Org. Chem., 1975, 40, 894 CrossRef CAS.
  17. H. Behringer and H. Waissauer, Chem. Ber., 1952, 85, 743 CAS.
  18. T. L. Gilchrist and P. D. Kemmitt, Tetrahedron, 1997, 53, 4447 CrossRef CAS.
  19. J. Becher, K. Pluta, N. Krake, K. Brondum, N. J. Christensen and M. V. Vinader, Synthesis, 1989, 7, 530 CrossRef.
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