New synthesis of model dihydroazepine-fused indolo[2,3-c]quinolines

Heterocycles

Volumn 60, Issue 1, 2003, Pages 73-87

  Al Khashashneh, Adel M ^a   El Abadelah, Mustafa M ^a   Boese, Roland ^b  

^a UNIVERSITY OF JORDAN   (Jordan)

^b UNIVERSITY OF DUISBURG ESSEN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

3 (2,6 DINITRO 4 TRIFLUOROMETHYLPHENYL)INDOLE; 3 DIAMINOPHENYLINDOLE; 7,8 DIHYDRO 1,12 IMINOBENZO[C]PYRIDO[4,3,2 EF][1]BENZAZEPINE; BENZAZEPINE DERIVATIVE; DIHYDROAZEPINE; INDOLOQUINOLINE DERIVATIVE; INDOLO[2,3 C]QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STRUCTURE ANALYSIS; SYNTHESIS; X RAY DIFFRACTION;

EID: 0037249617     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-02-9607     Document Type: Article

References (37)

1. (a) K. Staurt and R. Woo-Ming, Heterocycles, 1975, 3, 223.
2. (b) M. Julia, J. Bagot, and O. Siffert, Bull. Soc. Chim Fr., 1973, 1424.
3. (c) J. Bergman, Acta Chem. Scand., 1971, 25, 3296.
4. (d) J. Degraw, J. G. Kennedy, and W. A. Skinner, J. Med. Chem., 1967, 10, 127.
5. (a) J. Sandrin, D. Soerens, P. Mokry, and J. M. Cook, Heterocycles, 1977, 6, 1133.
6. (b) D. Soerens, J. Sandrin, F. Ungemach, P. Mokry, G. S. Wu, E. Yamanaka, L. Hutchins, M. DiPierro, and J. M. Cook, J. Org. Chem., 1979, 44, 535.
7. (a) L. Deng, K. M. Czerwinski, and J. M. Cook, Tetrahedron Lett., 1991, 32, 175.
8. (b) K. M. Czerwinski, L. Deng, and J. M. Cook, Tetrahedron Lett., 1992, 33, 4721.
9. E. D. Cox and J. M. Cook, Chem. Rev., 1995, 95, 1797.
10. (a) P. D. Bailey, S. P. Hollinshead, N. R. McLay, K. Morgan, S. J. Palmer, S. N. Prince, C. D. Reynolds, and S. D. Wood, J. Chem. Soc., Perkin Trans. I, 1993, 431.
11. (b) G. Casnati, A. Dossena, and A. Pochini, Tetrahedron Lett., 1972, 5277.
12. (c) A. H. Jackson, B. J. Naidoo, and P. Smith, Tetrahedron, 1968, 24, 6119.
13. S-I. Nakatsuka, H. Miyazaki, and T. Goto, Tetrahedron Lett., 1986, 27, 4757.
14. (a) G. S. King, P. G. Mantle, C. A. Szczyrbak, and E. S. Waight, Tetrahedron Lett., 1973, 215.
15. (b) G. S. King, E. S. Waight, P. G. Mantle, and C. A. Szczyrbak, J. Chem. Soc., Perkin Trans. I, 1977, 2099.
16. (c) D. A. Boyles and D. E. Nichols, J. Org. Chem., 1988, 53, 5128.
17. (d) M. Iwao and F. Ishibashi, Tetrahedron, 1997, 53, 51.
18. (e) Y. Yokoyama, T. Matsumoto, and Y. Murakami, J. Org. Chem., 1995, 60, 1486.
19. (f) M. Somei, S. Hamamoto, K. Nakagawa, F. Yamada, and T. Ohta, Heterocycles, 1994, 37, 719.
20. (g) L. Novák, M. Hanania, P. Kovács, J. Rohály, P. Kolonits, and C. Szántay, Heterocycles, 1997, 45, 2331.
21. (a) R. I. Fryer, R. Y. F. Ning, L. H. Sternbach, and A. Walser (Hofmann-La Roche, Inc.), Swiss Patent CH 602 728 (1978), 6 pp (Chem. Abstr., 1978, 89, 146890z).
22. (b) R. I. Fryer, R. Y. F. Ning, L. H. Sternbach, and A. Walser, US Patent 4, 014, 883 (1977), 26 pp (Chem. Abstr., 1977, 87, 39450t).
23. (c) N. Strojny, L. D'Arconte, and J. A. F. de Silva, J. Chromatogr., 1981, 223, 111.
24. (d) E. Grunberg, M. J. Kramer, M. Buch, and P. W. Trown, Chemotherapy, 1978, 24, 77.
25. (e) A. Walser, G. Silverman, T. Flynn, and R. I. Fryer, J. Heterocycl. Chem., 1975, 12, 351.
26. (a) R. A. Abramouvitch and I. D. Spenser, "Advanced Heterocyclic Chemistry: The β-Carbolines", Vol. 3, ed. by A. R. Katritzky, A. J. Boulton, and J. M. Lagowski, Academic Press, New York, 1964, pp. 79-207.
27. (b) A. Brossi, "The alkaloids", Vol. XXH, Academic Press, New York, 1983, Chapters 1 and 4.
28. (c) B. J. Baker, "Alkaloids: Chemical and Biological Perspectives", Vol. 10, ed. by W. Pelletier, Pergmon Press, Oxford, 1996, pp. 357-407.
29. For the preparation of N-indolylmetal salts and their utilization in the synthesis of 3-(heteroaryl)-indoles, see: (a) R. A. Heacock and S. Kǎspárek, "Advances in Heterocyclic Chemistry: The Indole Grignard Reagents", Vol. 10, ed. by A. R. Katritzky and A. J. Boulton, Academic Press, New York, 1969, pp. 43-112. (b) J. Bergman and L. Venemalm, Tetrahedron, 1990, 46, 6061. (c) W. A. Ayer, P. A. Craw, Y-T. Ma, and S. Mialo, Tetrahedron, 1992, 48, 2919. (d) K. A. Abu Safieh, M. M. El-Abadelah, S. S. Sabri, M. H. Abu Zarga, W. Voelter, and C. M.-Mössmer, J. Heterocycl. Chem., 2001, 38, 623, and references cited therein.
30. For the preparation of N-indolylmetal salts and their utilization in the synthesis of 3-(heteroaryl)-indoles, see: (a) R. A. Heacock and S. Kǎspárek, "Advances in Heterocyclic Chemistry: The Indole Grignard Reagents", Vol. 10, ed. by A. R. Katritzky and A. J. Boulton, Academic Press, New York, 1969, pp. 43-112. (b) J. Bergman and L. Venemalm, Tetrahedron, 1990, 46, 6061. (c) W. A. Ayer, P. A. Craw, Y-T. Ma, and S. Mialo, Tetrahedron, 1992, 48, 2919. (d) K. A. Abu Safieh, M. M. El-Abadelah, S. S. Sabri, M. H. Abu Zarga, W. Voelter, and C. M.-Mössmer, J. Heterocycl. Chem., 2001, 38, 623, and references cited therein.
31. For the preparation of N-indolylmetal salts and their utilization in the synthesis of 3-(heteroaryl)-indoles, see: (a) R. A. Heacock and S. Kǎspárek, "Advances in Heterocyclic Chemistry: The Indole Grignard Reagents", Vol. 10, ed. by A. R. Katritzky and A. J. Boulton, Academic Press, New York, 1969, pp. 43-112. (b) J. Bergman and L. Venemalm, Tetrahedron, 1990, 46, 6061. (c) W. A. Ayer, P. A. Craw, Y-T. Ma, and S. Mialo, Tetrahedron, 1992, 48, 2919. (d) K. A. Abu Safieh, M. M. El-Abadelah, S. S. Sabri, M. H. Abu Zarga, W. Voelter, and C. M.-Mössmer, J. Heterocycl. Chem., 2001, 38, 623, and references cited therein.
32. For the preparation of N-indolylmetal salts and their utilization in the synthesis of 3-(heteroaryl)-indoles, see: (a) R. A. Heacock and S. Kǎspárek, "Advances in Heterocyclic Chemistry: The Indole Grignard Reagents", Vol. 10, ed. by A. R. Katritzky and A. J. Boulton, Academic Press, New York, 1969, pp. 43-112. (b) J. Bergman and L. Venemalm, Tetrahedron, 1990, 46, 6061. (c) W. A. Ayer, P. A. Craw, Y-T. Ma, and S. Mialo, Tetrahedron, 1992, 48, 2919. (d) K. A. Abu Safieh, M. M. El-Abadelah, S. S. Sabri, M. H. Abu Zarga, W. Voelter, and C. M.-Mössmer, J. Heterocycl. Chem., 2001, 38, 623, and references cited therein.
33. J. A. Cowan, Tetrahedron Lett., 1986, 27, 1205. See also: H. V. Patel, K. A. Vyas, S. P. Pandey, and P. S. Fernandes, Organic Preparations and Procedures Int., 1995, 27, 81.
34. J. A. Cowan, Tetrahedron Lett., 1986, 27, 1205. See also: H. V. Patel, K. A. Vyas, S. P. Pandey, and P. S. Fernandes, Organic Preparations and Procedures Int., 1995, 27, 81.
35. The pentacyclic skeleton of 9a,b is also named, by the hetero-substitution (replacement) method, as follows: 5,6-dihydro-1H-1,6,10-triazabenzo[ij]naphtha[2,1,8-cde]azulene.
36. R. H. Blessing, Acta Crystallogr., 1995, A51, 33.
37. G. M. Sheldrick, SHELXTL PLUS System of computer programs for the determination of crystal structure from the X-Ray diffraction data, Vers.5.10.DOS/WN 95/NT.