Abstract
Data on methods for the construction of tetracyclic systems in which an isoindole ring is condensed with benzazepines and benzazocines on the [1,2] side are reviewed. The reaction conditions and approaches leading to isoindolobenzazepines and isoindolobenzazocines are discussed. Examples of the synthesis of physiologically active natural alkaloids with the structure of the above-mentioned condensed isoindoles are presented. Data for 1959–2004 are included.
Article PDF
Similar content being viewed by others
References
P. Pigeon and B. Decroix, Synth. Commun., 28, 2507 (1998).
G. N. Walker, A. R. Engle, and R. J. Kempton, J. Org. Chem., 37, 3755 (1972).
H. Heaney and K. F, Shuhaibar, Synlett, 47 (1995).
M. T. El Gihani, H. Heaney, and K. F. Shuhaibar, Synlett, 871 (1996).
P. Pigeon and B. Decroix, Tetrahedron Lett., 38, 1041 (1997).
Y. Ishihara, Y. Kiyota, and G. Goto, Chem. Pharm. Bull., 38, 3024 (1990).
A. Dalch, S. Marchalin, P. Pigeon, and B. Decroix, Tetrahedron Lett., 39, 9187 (1998).
Y. Ishihara, T. Tanaka, S. Miwatashi, A. Fujishima, and G. Goto, J. Chem. Soc., Perkin Trans. 1, 2993 (1994).
A. Chihab-Eddine, A. Daich, A. Wale, and B. Decroix, Heterocycles, 58, 449 (2002).
Y. Ishihara, T. Doi, H. Nagabukuro, and Y. Ishichi, WO Pat. 00/18391; http://v3.espacenet.com/origdoc?DB=EPODOC&IDX=WO0018391&F=0&QPN=WO00183 91
Y. Ishihara, Y. Fujisawa, and N. Furuyama, WO Pat. 9846590; Chem. Abstr., 129, 330744 (1998).
G. Goto, Y. Ishihara, and M. Miyamoto, EP Pat. 655451; Chem. Abstr., 123, 198832 (1995).
G. Goto and Y. Ishihara, Jpn. Pat. 02042078; Chem. Abstr., 113, 40431 (1990).
C. Schöpf and M. Schweickert, Chem. Ber., 99, 2566 (1965).
E. Valencia, I. Weiss, S. Firdous, A. J. Freyer, M. Shamma, A. Urzsa, and V. Fajardo, Tetrahedron, 40, 3957 (1984).
V. Fajardo, V. Elango, B. K. Cassels, and M. Shamma, Tetrahedron Lett., 23, 39 (1982).
E. Valencia, A. J. Freyer, M. Shamma, and V. Fajardo, Tetrahedron Lett., 25, 599 (1984).
J. Fuska, A. Fuskovi, and B. Proksa, Pharmazie, 37, 443 (1982).
B. Proksa and J. Fuska, Pharmazie, 40, 521 (1985).
V. Scartoni, R. Fiaschi, S. Catalano, I. Morelli, and A. Marsili, J. Chem. Soc., Perkin Trans. 1, 1547 (1979).
P. L. Barili, R. Fiaschi, E. Napolitano, L. Pistelli, V. Scartoni, and A. Marsili, J. Chem. Soc., Perkin Trans. 1, 1654 (1981).
E. Napolitano, R. Fiaschi, V. Scartoni, and A. Marsili, J. Chem. Soc., Perkin Trans. 1, 781 (1986).
E. Napolitano, G. Spinelli, R. Fiaschi, and A. Marsili, J. Chem. Soc., Perkin Trans. 1, 785 (1986).
A. Couture, E. Deniau, P. Grandclaudon, and C. Hoarau, Tetrahedron, 56, 1491 (2000).
Y. Koseki and T. Nagasaka, Chem. Pharm. Bull., 43, 1604 (1995).
A. Marsili, V. Scartoni, I. Morelli, and P. Pierangeli, J. Chem. Soc., Perkin Trans. 1, 959 (1977).
H. O. Bernhard and V. Snieckus, Tetrahedron Lett., 4867 (1971).
G. Kim, J. H. Kim, W.-J. Kim, and Y. A. Kim, Tetrahedron Lett., 44, 8207 (2003).
G. Rodriguez, M. M. Cid, C. Sai, L. Castedo, and D. Dominguez, J. Org. Chem., 61, 2780 (1996).
M. M. Cid, D. Domknguez, L. Castedo, E. M. Vizquez-Lopez, Tetrahedron, 55, 5599 (1999).
H. Yoda, A. Nakahama, T. Koketsu, and K. Takabe, Tetrahedron Lett., 43, 4667 (2002).
P. H. Mazzocchi, C. R. King, and H. L. Amnion, Tetrahedron Lett., 28, 2473 (1987).
M. Machida, M. Nakamura, K. Oda, H. Takechi, K. Ohno, H. Nakai, Y. Sato, and Y. Kanaoka, Heterocycles, 26, 2683 (1987).
H. Ishibashi, H. Kawanami, H. Iriyama, and M. Ikeda, Tetrahedron Lett., 36, 6733 (1995).
H. Ishibashi, H. Kawanami, and M. Ikeda, J. Chem. Soc., Perkin Trans. 1, 817 (1997).
J. Trojanek, Z. Koblicova, V. Suchan, and J. Holubek, Collect. Czech. Chem. Commun., 40, 681 (1975).
B. Proksa, Z. Votickz, and M. Stefek, Chem. Zvesti, 34, 248 (1980).
B. Proska, J. Fuska, Z. Voticky, Pharmazie, 37, 350 (1982).
A. Garcia, D. Rodriguez, L. Castedo, C. Sai, and D. Dominguez, Tetrahedron Lett., 42, 1903 (2001).
S. Ruchirawat, W. Lertwanawatana, S. Thianpatanagul, J. L. Cashaw, and V. E. Davis, Tetrahedron Lett., 25, 3485 (1984).
J. Chiefari, W. K. Janowski, and R. H. Prager, Tetrahedron Lett., 27, 6119 (1986).
J. Chiefari, W. K. Janowski, and R. H. Prager, Aust. J. Chem., 42, 49 (1989).
S. V. Kessar, T. Singh, and R. Vohra, Tetrahedron Lett., 28, 5323 (1987).
S. V. Kessar, T. Singh, and R. Vohra, Ind. J. Chem., 30B, 99 (1991).
F. G. Fang and S. J. Danishefsky, Tetrahedron Lett., 30, 2747 (1989).
S. Ruchirawat and P. Sahakitpichan, Tetrahedron Lett., 41, 8007 (2000).
W. Klötzer, S. Teitel, J. F. Blount, and A. Brossi, J. Am. Chem. Soc., 93, 4321 (1971).
W. Klötzer, S. Teitel, and A. Brossi, Helv. Chim. Acta, 54, 2057 (1971).
R. Hohlbrugger, W. Klötzer, Chem. Ber., 107, 3457 (1974).
S. Teitel, W. Klötzer, J. Borgese, and A. Brossi, Can. J. Chem., 50, 2022 (1972).
C. J. Moody and G. J. Warrellow, J. Chem. Soc., Perkin Trans. 1, 2929 (1990).
C. J. Moody and G. J. Warrellow, Tetrahedron Lett., 28, 6089 (1987).
S. Yasuda, Y.-I. Sugimoto, C. Mukai, and M. Hanaoka, Heterocycles, 30, 335 (1990).
J. R. Fuchs and R. L. Funk, Org. Lett., 3, 3923 (2001).
D. Walterova and F. Santava, Collect. Czech. Chem. Commun., 35, 1623 (1968).
M. Shamma, The Isoquinoline Alkaloids, Academic Press, New York (1972).
J. L. Moniot, D. M. Hindenlang, and M. Shamma, J. Org. Chem., 44, 4343 (1979).
G. Manikumar and M. Shamma, Heterocycles, 14, 827 (1980).
C. K. Dorn, F. J. Koszyk, and G. R. Lenz, J. Org. Chem., 49, 2642 (1984).
J. L. Moniot, D. M. Hindenlang, and M. Shamma, J. Org. Chem., 44, 4347 (1979).
M. Shamma, J. L. Moniot, and D. M. Hindenlang, Tetrahedron Lett., 4273 (1977).
V. Elango and M. Shamma, J. Org. Chem., 48, 4879 (1983).
C. Lamas, C. Saa, L. Castedo, and D. Domknguez, Tetrahedron Lett., 33, 5653 (1992).
G. Rodrkguez, L. Castedo, D. Domknguez, and C. Sai, Tetrahedron Lett., 39, 6551 (1998).
G. Rodrkguez, L. Castedo, D. Domknguez, C. Sai, W. Adam, and C. R. Saha-Möller, J. Org. Chem., 64, 877 (1999).
A. Padwa, L. S. Beall, C. K. Eidell, and K. J. Worsencroft, J. Org. Chem., 66, 2414 (2001).
Y. Koseki, S. Kusano, H. Sakata, and T. Nagasaka, Tetrahedron Lett., 40, 2169 (1999).
Y. Koseki, S. Katsura, S. Kusano, H. Sakata, H. Sato, Y. Monzene, and T. Nagasaka, Heterocycles, 59, 527 (2003).
H. Heaney and K. F. Shuhaibar, Tetrahedron Lett., 35, 2751 (1994).
F. I. Zubkov, E. V. Boltukhina, A. P. Krapivko, and A. V. Varlamov, Khim. Geterotsikl. Soedin., 1737 (2003). [Chem. Heterocycl. Compd., 39, 1534 (2003)]
F. I. Zubkov, E. V. Boltukhina, K. F. Turchin, and A. V. Varlamov, Tetrahedron, 60, 8455 (2004).
E. Valencia, V. Fajardo, A. J. Freyer, and M. Shamma, Tetrahedron Lett., 26, 993 (1985).
M. Shamma and M. Rahimizadeh, J. Nat. Prod., 49, 398 (1986).
R. Yoneda, Y. Sakamoto, Y. Oketo, K. Minami, S. Harusawa, and T. Kurihara, Tetrahedron Lett., 35, 3749 (1994).
Author information
Authors and Affiliations
Additional information
__________
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 963–994, July, 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. 1. Isoindolobenzazepines, isoindolobenzazocines. (Review). Chem Heterocycl Compd 42, 831–857 (2006). https://doi.org/10.1007/s10593-006-0169-0
Received:
Issue Date:
DOI: https://doi.org/10.1007/s10593-006-0169-0