A new ring system: 3-H-pyrazolo[3,4-h]isoquinoline. An unexpected product from diazotization of an aminoisoquinoline

Chemical Communications

Volumn , Issue 24, 1996, Pages 2711-2712

  Miller, R Bryan ^a   Stowell, Joseph G ^a   Jenks, Christopher W ^a   Farmer, Steven C ^a   Wujcik, Chad E ^a   Olmstead, Marilyn M ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 1542605944     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/cc9960002711     Document Type: Article

References (19)

1. For reviews, see: G. W. Gribble, in The Alkaloids, ed. A. Brossi, Academic, New York, 1990, vol. 39, pp. 239-352; C. J. Moody, Synlett, 1994, 681.
2. For reviews, see: G. W. Gribble, in The Alkaloids, ed. A. Brossi, Academic, New York, 1990, vol. 39, pp. 239-352; C. J. Moody, Synlett, 1994, 681.
3. For some recent approaches to ellipticines, see: 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; G. W. Gribble, M. G. Saulnier, J. A. Obaza-Nutaitis and D. M. Ketcha, J. Org. Chem., 1992, 57, 5891; A. Godard, F. Marsais, N. Ply, F. Trecourt, A. Turck and G. Queguiner, Heterocycles, 1995, 40, 1055; I. Minoru, J. Chem. Soc., Chem. Commun., 1995, 409.
4. For some recent approaches to ellipticines, see: 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; G. W. Gribble, M. G. Saulnier, J. A. Obaza-Nutaitis and D. M. Ketcha, J. Org. Chem., 1992, 57, 5891; A. Godard, F. Marsais, N. Ply, F. Trecourt, A. Turck and G. Queguiner, Heterocycles, 1995, 40, 1055; I. Minoru, J. Chem. Soc., Chem. Commun., 1995, 409.
5. For some recent approaches to ellipticines, see: 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; G. W. Gribble, M. G. Saulnier, J. A. Obaza-Nutaitis and D. M. Ketcha, J. Org. Chem., 1992, 57, 5891; A. Godard, F. Marsais, N. Ply, F. Trecourt, A. Turck and G. Queguiner, Heterocycles, 1995, 40, 1055; I. Minoru, J. Chem. Soc., Chem. Commun., 1995, 409.
6. For some recent approaches to ellipticines, see: 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; G. W. Gribble, M. G. Saulnier, J. A. Obaza-Nutaitis and D. M. Ketcha, J. Org. Chem., 1992, 57, 5891; A. Godard, F. Marsais, N. Ply, F. Trecourt, A. Turck and G. Queguiner, Heterocycles, 1995, 40, 1055; I. Minoru, J. Chem. Soc., Chem. Commun., 1995, 409.
7. For approaches from our laboratories, see: (a) R. B. Miller and T. Moock, Tetrahedron Lett., 1980, 21, 3319; (b) R. B. Miller and J. G. Stowell, J. Org. Chem., 1983, 48, 886; (c) R. B. Miller and S. Dugar, Tetrahedron Lett., 1989, 30, 297.
8. For approaches from our laboratories, see: (a) R. B. Miller and T. Moock, Tetrahedron Lett., 1980, 21, 3319; (b) R. B. Miller and J. G. Stowell, J. Org. Chem., 1983, 48, 886; (c) R. B. Miller and S. Dugar, Tetrahedron Lett., 1989, 30, 297.
9. For approaches from our laboratories, see: (a) R. B. Miller and T. Moock, Tetrahedron Lett., 1980, 21, 3319; (b) R. B. Miller and J. G. Stowell, J. Org. Chem., 1983, 48, 886; (c) R. B. Miller and S. Dugar, Tetrahedron Lett., 1989, 30, 297.
10. R. B. Miller, S. Dugar and J. R. Epperson, Heterocycles, 1987, 25, 217; A. N. Fujiwara, E. M. Acton and L. Goodman, J. Med. Chem., 1967, 10, 126.
11. R. B. Miller, S. Dugar and J. R. Epperson, Heterocycles, 1987, 25, 217; A. N. Fujiwara, E. M. Acton and L. Goodman, J. Med. Chem., 1967, 10, 126.
12. R. B. Miller and J. M. Frincke, J. Org. Chem., 1980, 45, 5312.
13. J. H. Uhlenbroek and M. Slagt, Recl. Trav. Chim. Pay. Bas., 1961, 80, 1057.
14. A. N. Fujiwara, E. M. Acton and L. Goodman, J. Heterocycl. Chem., 1968, 5, 853.
15. R. Pschorr, Ber., 1896, 29, 496; A. F. Hegarty, in The Chemistry of the Functional Groups, ed. S. Patai, Wiley, New York, 1978, pp. 561-64; K. H. Saunders and R. L. M. Allen, Aromatic Diazo Compounds, 3rd edn., Edward Arnold, London, 1985, p. 640.
16. R. Pschorr, Ber., 1896, 29, 496; A. F. Hegarty, in The Chemistry of the Functional Groups, ed. S. Patai, Wiley, New York, 1978, pp. 561-64; K. H. Saunders and R. L. M. Allen, Aromatic Diazo Compounds, 3rd edn., Edward Arnold, London, 1985, p. 640.
17. R. Pschorr, Ber., 1896, 29, 496; A. F. Hegarty, in The Chemistry of the Functional Groups, ed. S. Patai, Wiley, New York, 1978, pp. 561-64; K. H. Saunders and R. L. M. Allen, Aromatic Diazo Compounds, 3rd edn., Edward Arnold, London, 1985, p. 640.
18. For formation of pyrazolo heterocycles from aryl diazonium salts, see: R. N. Butler, Chem. Rev., 1975, 75, 241; H. Suschitzky, Angew. Chem., Int. Ed. Engl. 1967, 6, 596.
19. For formation of pyrazolo heterocycles from aryl diazonium salts, see: R. N. Butler, Chem. Rev., 1975, 75, 241; H. Suschitzky, Angew. Chem., Int. Ed. Engl. 1967, 6, 596.