An Alternative Synthesis of 10H-Indolo[3,2-b]quinoline and its Selective N- Alkylation

Journal of Heterocyclic Chemistry

Volumn 34, Issue 6, 1997, Pages 1789-1794

  Fan, Pingchen ^a   Ablordeppey, Seth Y ^a  

^a FLORIDA A AND M UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

10H INDOLO[3,2 B]QUINOLINE; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CHEMICAL REACTION; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; MEDICINAL PLANT; PLANT;

EID: 0031418357     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570340624     Document Type: Article

References (27)

1. M. M. Cooper, J. M. Lovell and J. A. Joule, Tetrahedron Letters, 37, 4283 (1996).
2. K. Cimangi, T. D. Bruyne, L. Pieters, M. Claeys and A. Vlietinck, Tetrahedron Letters, 37, 1703 (1996).
3. D. Dwuma-Badu, J. S. K. Ayim, N. I. Y. Fiagbe, J. E. Knapp, D. L. Schiff, Jr. and D. J. Slatkin, J. Pharm. Sci., 67, 433 (1978).
4. K. Cimanga, T. D. Bruyne, A. Lawre, B. V. Poel, L. Pieters, M. Claeys, D.-V. Berghe, K. Kambu, L. Tona and A. J. Vlietinck, Planta Med., 62, 22 (1996).
5. M. Singh, M. P. Singh and S. Y. Ablordeppey, Drug. Dev. Ind. Pharm., 22, 379 (1996).
6. K. Boakye-Yiadom and S. M. Herman Ackah, J. Pharm. Sci., 68, 1510 (1979).
7. A. O. Oyekan and S. Y. Ablordeppey, Med. Chem. Res., 6, 602 (1996).
8. S. J. Holt and V. Petrow, J. Chem. Soc., 607 (1946).
9. [9a] K. Gorlitzer and J. Weber, Arch, Pharm. (Weinheim), 314, 852 (1981);
10. [b] M. Yamato, Y. Takeuchi, M. Chang and K. Hashigaki, Chem. Pharm. Bull., 40, 528 (1992);
11. [c] Y. Takeuchi, M. Chang, K. Hashigaki, T. Tashiro, T. Tsuruo, S. Tsukagoshi and M. Yamato, Chem. Pharm. Bull., 40, 1481 (1992).
12. D. E. Bierer, D. M. Fort, C. D. Mendez, J. Luo, P. Peterli-Roth, L. G. Dubenko, R. E. Gerber, J. Litvak, Q. Lu, P. Zhang, M. J. Reed, N. Waldeck, R. C. Bruening, B. K. Noamesi, R. F. Hector, T. J. Carlson and S. R. King, Poster MED 131, 213th American Chemical Society Meeting, San Francisco, CA April 13, 1997.
13. D. H. R. Barton, J.-P. Finet and J. Khamsi, Tetrahedron Letters, 27, 3615 (1986).
14. D. H. R. Barton, J.-P. Finet and J. Khamsi, Tetrahedron Letters, 28, 887 (1987).
15. B. Akermark, L. Eberson, E. Jonsson and E. Pettersson, J. Org. Chem., 40, 1365 (1975).
16. [14a] E. C. Taylor, J. G. Andrade, G. J. H. Rail and A. McKillop, J. Am. Chem. Soc., 102, 6513 (1980);
17. [b] R. C. Gambie, M. G. Dunlop, P. S. Rutledge and P. D. Woodgate, Synth. Commun., 10, 827 (1980);
18. [c] G. Brigmann, R. Walter, R. Weirich, Angew. Chem., Int. Ed. Engt., 29, 977 (1990).
19. V. M. Dark, A. Cox and E. J. Herbert, J. Chem. Soc. (C), 831 (1968).
20. R. B. Miller and T. Moock, Tetrahedron Letters, 21, 3319 (1980).
21. [17a] G. B. Bachman, D. E. Welton, G. L. Jenkins and J. E. Christian, J. Am. Chem. Soc., 69, 365 (1947);
22. [b] A. R. Surrey and R. A. Cutler, J. Am. Chem. Soc., 73, 2413 (1951);
23. [c] K. Schofield and R. S. Theobald, J. Chem. Soc., 395 (1950);
24. [d] G. C. Wright, J. E. Gray and C-N. Yu, J. Med Chem., 17, 244 (1974).
25. [18a] G. F. Duffin, Adv. Heterocyclic Chem., 3, 1 (1964);
26. [b] L. W. Deady, D. C. Stillman, Aust. J. Chem., 29, 1745 (1976).
27. J. Degutis and A. Ezerskaite, Khim. Geterotsükl Soedin., 1375 (1986).