Abstract
Data for 1966–2004 on methods for the construction of tetracyclic systems in which an isoindole ring is condensed with quinoline and isoquinoline fragments on the [1,2] side are reviewed. Methods and conditions for the synthesis of isoindoloquinolines and isoindoloisoquinolines are examined. Examples of the synthesis of physiologically active natural alkaloids possessing the structure of these condensed isoindoles are presented.
Similar content being viewed by others
References
Y. Ishihara, Y. Kiyota, and G. Goto, Chem. Pharm. Bull., 38, 3024 (1990).
Z. Sui, J. Altom, V. N. Nguyen, J. Fernandez, J. I. Bernstein, J. J. Hiliard, J. F. Barrett, B. L. Podlogar, and K. A. Ohemeng, Bioorg. Med. Chem., 6, 735 (1998).
J. Epsztajn, R. Grzelak, and A. Jozwiak, Synthesis, 1212 (1996).
J. Epsztajn, A. Jozwiak, P. Koluda, I. Sadokierska, and I. D. Wilkowska, Tetrahedron, 56, 4837 (2000).
G. Kim and G. Keum, Heterocycles, 45, 1979 (1997).
H. Z. Alkhathlan and K. A. Al-Farhan, Heterocycles, 48, 641 (1998).
Z. Hamersak, M. Litvic, D. Sepac, A. Lesac, Z. Raza, and V. Sunjic, Synthesis, 2174 (2002).
P. Kumar, C. U. Dinesh, and B. Pandey, Tetrahedron Lett., 35, 9229 (1994).
P. Pigeon and B. Decroix, Synth. Commun., 28, 2507 (1998).
P. Pigeon, M. Othman, P. Netchitailo, and B. Decroix, J. Heterocycl. Chem., 36, 691 (1999).
W. H N. Nijhuis, G. R. B. Leus, R. J. M. Egberink, W. Verboom, and D. N. Reinhoudt, Rec. Trav. Chim. Pays-Bas, 108, 172 (1989).
F. I. Zubkov, E. V. Boltukhina, K. F. Turchin, R. S. Borisov, and A. V. Varlamov, Tetrahedron, 61, 4099 (2005).
A. V. Varlamov, F. I. Zubkov, E. V. Boltukhina, N. V. Sidorenko, and R. S. Borisov, Tetrahedron Lett., 44, 3641 (2003).
E. V. Boltukhina, F. I. Zubkov, E. V. Nikitina, and A. V. Varlamov, Synthesis, 1859 (2005).
F. I. Zubkov, E. V. Boltukhina, E. V. Nikitina, and A. V. Varlamov, Izv. Akad. Nauk. Ser. Khim., 2703 (2004).
Y. Abe, A. Ohsawa, and H. Igeta, Heterocycles, 19, 49 (1982).
D.-B. Reuschling and F. Kröhnke, Chem. Ber., 104, 2103 (1971).
L. N. Donchak, M. A. Zagoruiko, and V. A. Kaminskii, Zh. Org. Khim., 31, 1872 (1995).
M. A. Zagoruiko, L. N. Donchak, and V. A. Kaminskii, Zh. Org. Khim., 35, 146 (1999).
L. N. Donchak, V. A. Kaminskii, and M. N. Tilichenko, Khim. Geterotsikl. Soedin., 1271 (1986). [Chem. Heterocycl. Comp., 22, 1031 (1986)].
V. U. Ahmad and S. Iqbal, Phytochemistry, 33, 735 (1993).
S. Durrani and T. Rasheed, Fitoterapia, 172 (1995).
V. U. Ahmad, Atta-ur-Rahman, T. Rasheed, and Habib-ur-Rehman, Heterocycles, 26, 1251 (1987).
T. Rasheed, M. N. I. Khan, and S. S. A. Zhadi, J. Nat. Prod., 54, 582 (1991).
V. U. Ahmad and S. Iqbal, Nat. Prod. Lett., 2, 105 (1993); Chem. Abstr., 120, 265790 (1994).
E. Valencia, A. J. Freyer, M. Shamma, and V. Fajardo, Tetrahedron Lett., 25, 599 (1984).
G. Manikumar and M. Shamma, Heterocycles, 14, 827 (1980).
W. J. Houlihan and R. E. Manning, US Pat. 3644370; Chem. Abstr., 77, 34368 (1972).
W. J. Houlihan and R. E. Manning, US Pat. 3644369; Chem. Abstr., 77, 34376 (1972).
W. J. Houlihan and R. E. Manning, US Pat. 3686207; Chem. Abstr., 77, 152006 (1972).
J. L. Moniot, D. M. Hindenlang, and M. Shamma, J. Org. Chem., 44, 4347 (1979).
M. Winn and H. E. Zaugg, J. Org. Chem., 33, 3779 (1968).
R. Alonso, L. Castedo, and D. Dominguez, Tetrahedron Lett., 26, 2925 (1985).
G. J. Hitchings, M. Helliwell, and J. M. Vernon, J. Chem. Soc., Perkin Trans. 1, 83 (1990).
G. J. Hitchings and J. M. Vernon, J. Chem. Soc., Perkin Trans. 1, 1757 (1990).
H. Heaney and K. F. Shuhaibar, Synlett, 47 (1995).
M. T. El Gihani, H. Heaney, and K. F. Shuhaibar, Synlett, 871 (1996).
A. R. Katritzky, S. Mehta, and H.-Y. He, J. Org. Chem., 66, 148 (2001).
M. I. Collado, N. Sotomayor, M.-J. Villa, and E. Lete, Tetrahedron Lett., 37, 6193 (1996).
M. I. Collado, I. Manteca, N. Sotomayor, M.-J. Villa, and E. Lete, J. Org. Chem., 62, 2080, (1997).
A. Padwa, M. N. Jacquez, and A. Schmidt, Org. Lett., 3, 1781 (2001).
G. Kim, J. H. Kim, W.-J. Kim, and Y. A. Kim, Tetrahedron Lett., 44, 8207 (2003).
P. L. Barili and V. Scartoni, J. Heterocycl. Chem., 22, 1199 (1985).
G. N. Walker and R. J. Kempton, J. Org. Chem., 36, 1413 (1971).
S. M. Allin, C. J. Northfield, M. I. Page, and A. M. Z. Slawin, Tetrahedron Lett., 39, 4905 (1998).
R. Grigg, V. Sridharan, P. Stevenson, S. Sukirthalingam, and T. Worakun, Tetrahedron, 46, 4003 (1990).
B. Burns, R. Grigg, P. Ratananukul, V. Sridharan, P. Stevenson, and T. Worakun, Tetrahedron Lett., 29, 4329 (1988).
R. Grigg, V. Sridharan, P. Stevenson, and T. Worakun, J. Chem. Soc, Chem. Commun., 1697 (1986).
H. Heaney and K. F. Shuhaibar, Tetrahedron Lett., 35, 2751 (1994).
T. V. Alpatova and V. G. Yashunskii, Khim. Geterotsikl. Soedin., 1084 (1981). [Chem. Heterocycl. Comp., 17, 804 (1981)].
Y. Tominaga, Y. Shiroshita, Y. Matsuda, and A. Hosomi, Heterocycles, 26, 2073 (1987).
T. Kato, T. Chiba, and T. Sasaki, Yakugaku Zasshi, 99, 1051 (1979); Chem. Abstr., 92, 163827 (1980).
N. S. Basketter and A. O. Plunkett, J. Chem. Soc, Chem. Commun., 188 (1973).
W. Augstein and F. Krönke, Liebigs Ann. Chem., 697, 158 (1966).
M. Sainsbury, D. W. Brown, S. F. Dyke, and G. Hardy, Tetrahedron, 25, 1881 (1969).
A. Marsili and V. Scartoni, Gazz. Chim. Ital., 104, 165 (1974).
A. Marsili and V. Scartoni, Tetrahedron Lett., 2511 (1968).
M. Machida, M. Nakamura, K. Oda, H. Takechi, K. Ohno, H. Nakai, Y. Sato, and Y. Kanaoka, Heterocycles, 26, 2683 (1987).
Z. Koblicova, V. Suchan, and J. Trojanek, Czech. Pat. 167097; Chem. Abstr., 87, 168002 (1977).
V. Suchan, Z. Koblicova, and J. Trojanek, Czech. Pat. 167096; Chem. Abstr., 87, 168003 (1977).
M. K. Eberle, L. Brzechffa, and W. J. Houlihan, J. Org. Chem., 42, 894 (1977).
V. I. Ognyanov, M. A. Haimova, and N. M. Mollov, Monatsh. Chem., 113, 993 (1982).
J. H. Brewster and S. Jones, Jr., J. Org. Chem., 34, 354 (1969).
R. Yamaguchi, T. Hamasaki, and K. Utimoto, Chem. Lett., 913 (1988).
I. F. Barnard and J. A. Elvidge, J. Chem. Soc., Perkin Trans. 1, 1813 (1983).
S. Wawzonek, J. K. Stowell, and R. E. Karll, J. Org. Chem., 31, 1004 (1966).
D. J. Brickwood, A. M. Hassan, W. D. Ollis, J. S. Stephanatou, and J. F. Stoddart, J. Chem. Soc., Perkin Trans. 1, 1393 (1978).
A. Garcia, D. Rodriguez, L. Castedo, C. Saa, and D. Dominguez, Tetrahedron Lett., 42, 1903 (2001).
J. C. Godfrey, J. Org. Chem., 24, 581 (1959).
E. V. Boltukhina, F. I. Zubkov, and A. V. Varlamov, Khim. Geterotsikl. Soedin., 963 (2006). [Chem. Heterocycl. Comp., 42, 831 (2006)].
Author information
Authors and Affiliations
Additional information
__________
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1123–1157, August, 2006.
Rights and permissions
About this article
Cite this article
Boltukhina, E.V., Zubkov, F.I. & Varlamov, A.V. Methods for the construction of [1,2]isoindolo-condensed benzazepines, benzazocines, quinolines, and isoquinolines. 2. Isoindoloquinolines, isoindoloisoquinolines. (Review). Chem Heterocycl Compd 42, 971–1001 (2006). https://doi.org/10.1007/s10593-006-0193-0
Received:
Issue Date:
DOI: https://doi.org/10.1007/s10593-006-0193-0