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DOI: 10.1039/A901521C (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 1, 1999, 2183-2188

Fused quinoline heterocycles I. First example of the 2,4-diazidoquinoline-3-carbonitrile and 1-aryl-1,5-dihydro-1,2,3,4,5,6-hexaazaacephenanthrylenes ring systems

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Ramadan A. Mekheimer

Abstract

4-Alkylamino-2-chloroquinoline-3-carbonitriles 2a–f react with hydrazine hydrate to give, in each case, the corresponding 3-amino-4-hydrazino-1H-pyrazolo[3,4-b]quinoline 7. Diazotization of 7 leads to the formation of 2,4-diazidoquinoline-3-carbonitrile 8, a new heterocyclic ring system. The azidoquinoline 8 can be converted to the corresponding aminoquinolines 14, and 15 and 16, by reaction with morpholine and sodium dithionite, respectively. On the other hand, 3-amino-4-arylamino-1H-pyrazolo[3,4-b]quinolines 4g–j were prepared by reaction of 4-arylamino-2-chloroquinoline-3-carbonitriles 2g–j with hydrazine hydrate at 50–60 °C. Diazotization of 4g–j afforded the novel tetracyclic ring system 1-aryl-1,5-dihydro-1,2,3,4,5,6-hexaazaacephenanthrylenes 5g–j.

References

  1. R. Mekheimer, E. Kh. Ahmed and A. F. Kattab, Bull. Chem. Soc. Jpn., 1993, 66, 2936 CAS .
  2. R. Mekheimer, Pharmazie, 1994, 49, 486 Search PubMed .
  3. R. Mekheimer, Bull. Soc. Chim. Fr., 1994, 131, 279 CAS .
  4. R. Mekheimer, J. Chem. Res. (S), 1994, 304 Search PubMed .
  5. A. A. Hassan, R. Mekheimer and N. K. Mohamed, Pharmazie, 1997, 52, 589 Search PubMed .
  6. M. P. Wentland, S. C. Aldous, D. M. Gruett, R. B. Perni, R. G. Powles, D. W. Danz, K. M. Klingbeil, A. D. Peverly and R. G. Robinson, Bioorg. Med. Chem. Lett., 1995, 5, 405 CrossRef CAS .
  7. A. Afonso, J. M. Kelly and S. Chackalamannil, U.S. Pat., 5 608 067, 1997(Chem. Abstr., 1997, 126, 225297x) Search PubMed .
  8. A. Afonso, J. M. Kelly and S. Chackalamannil, U.S. Pat., 5 506 236, 1996(Chem. Abstr., 1996, 125, 33629q) Search PubMed .
  9. R. W. Baldwin, M. W. Partridge and M. F. G. Stevens, J. Pharm. Pharmacol., Suppl., 1966, 18, 1 Search PubMed .
  10. T. Endre, G. Melinda, F. Odon and J. Judit, Hung. Teljes H U 42 771, 1987(Chem. Abstr., 1988, 109, 73479s) Search PubMed .
  11. V. L. Rusinov, E. N. Ulomskii, O. N. Chupakhin, M. M. Zubairov, A. B. Kapustin, N. L. Mitin, M. L. Zhiravetskii and I. A. Vinograd, Khim-Farm. Zh., 1990, 24, 41 (Russian) (Chem. Abstr., 1991, 114, 143358f) Search PubMed .
  12. W. Steinschifter and W. Stadlbauer, J. Prakt. Chem., 1994, 336, 311 CAS .
  13. W. Stadlbauer, Monatsh. Chem., 1986, 117, 1305 CAS .
  14. Th. Kappe, P. F. Fritz and E. Ziegler, Chem. Ber., 1973, 106, 1927 CAS .
  15. G. M. Coppola and G. E. Hardtmann, J. Heterocycl. Chem., 1981, 18, 917 CAS .
  16. G. M. Coppola, A. D. Kahle and M. Shapiro, Org. Magn. Reson., 1981, 17, 242 Search PubMed .
  17. J. L. G. Ruano, C. Pedregal and J. H. Rodriguez, Heterocycles, 1991, 32, 2151 .
  18. K. Gewald, U. Hain, G. Schwarzer and M. Gruner, J. Prakt. Chem., 1992, 334, 89 CAS .
  19. S. B. Kadin and C. H. Lamphere, Synthesis, 1977, 500 CrossRef CAS .
  20. J. M. C. Golec, R. M. Scrowston and M. Dunleavy, J. Chem. Soc., Perkin Trans. 1, 1992, 239 RSC .
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