Abstract
N,N′,N″-Trialkyl-2,5-bis(1-aminoethyl)pyrroles, prepared by the heterocyclization of 1,8-dibromooctan-3,6-dione with aliphatic amines, underwent the Pictet-Spengler reaction with formaldehyde and aromatic aldehydes to give substituted 5H-1,2,3,4,6,7,8,9-octahydrodipyrido[4,3-b;3′,4′-d]pyrroles.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
A. Pictet and T. Spengler,Ber. 44, 2030 (1911).
W. M. Whaley and T. R. Govindachar, in:Organic Reactions, R. Adams (ed.), John Wiley and Sons, New York (1951), Vol 6, 151.
V. I. Dulenko, I. V. Komissarov, A. T. Dolzhenko, and Yu. A. Nikolyukin,β-Carbolines. Their Chemistry and Neurobiology, [in Russian], Naukova Dumka, Kiev (1992), p. 4.
E. D. Cox and J. M. Cook,Chem. Rev.,95, 1797 (1995).
W. Herz and S. Tocker,J. Am. Chem. Soc.,77, 6353 (1955).
T. N. Borisova, A. V. Varlamov, N. D. Sergeeva, A. T. Soldatenkov, O. V. Zvolinsky, A. A. Astakhov, and N. S. Prostakov,Khim. Geterotsikl. Soedin., No. 7, 973 (1987).
A. N. Yakhontov,Usp. Khim.,49, 840 (1980).
A. N. Kost, M. A. Yurovskaya, and F. A. Trofimov,Khim. Geterotsikl. Soedin., No. 3, 291 (1973).
L. Kaczmarek, A. Beckalski, and P. Nantka-Namirski,Pol. J. Chem.,54, 1585 (1980).
Nguyen Chi Hung and E. Bisagni,Tetrahedron,42, 2303 (1986).
Nguyen Chi Hung, E. Bisagni, O. Pepin, A. Pierre, and P. De Cointet,J. Med. Chem.,30, 1642 (1987).
V. Pierson, A. Pierre, P. De Cointet, Nguyen Chi Hung, E. Bisagni, and P. Gros,Biochem. Pharmacol.,38, 1395 (1989).
D. A. Vasilevskii, S. V. Sviridov, and O. G. Kulinkovich,Zh. Org. Khim.,27, No. 10, 2132 (1991).
O. G. Kulinkovich and V. V. Bagutsky,Zh. Org. Khim.,33, No. 6, 898 (1997).
R. A. Jones and G. P. Bean,The Chemistry of Pyrroles. Academic Press, London (1969), p. 77.
J. M. Patterson and S. Soedigo,J. Org. Chem.,33, 4033 (1968).
L.-H. Zhang and J. Cook,Heterocycles,27, 1357 (1988).
D. Soerens, J. Sandrin, F. Ungemach, P. Mokry, G. S. Wu, E. Yamanaka, L. Hutchins, M. D. Pierro, and J. M. Cook,J. Org. Chem.,44, 535 (1979).
M. Jawdosiuk and J. Cook,J. Org. Chem.,49, 2699 (1984).
Author information
Authors and Affiliations
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, 617–622, May, 2000.
Rights and permissions
About this article
Cite this article
Bagutsky, V.V., Kulinkovich, O.G. Synthesis of substituted 5H-1,2,3,4,6,7,8,9-octahydrodipyrido-[4,3-b;3′,4′-d]pyrroles by the Pictet-Spengler condensation. Chem Heterocycl Compd 36, 537–541 (2000). https://doi.org/10.1007/BF02290840
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF02290840