Abstract
Reaction of 2-acetylpyridine with 4-[2.2]paracyclophanyllithium or 4-acetyl[2.2]paracyclophane with 2-pyridllithium gives 1-([2.2]paracyclophan-4-yl)-1-(2-pyridyl)ethanol. Its molecular and crystalline structures have been studied by x-ray analysis. It was found that heating this alcohol in acid medium causes dehydration and heterocyclization to give 1-paracyclophanyl-1-pyridylethylene and 10-methyl[2.2]paracyclophano[4,5-bindolizine.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
A. T. Soldatenkov, N. M. Kolyadina, L. N. Kuleshova, and V. N. Khrustalev, Khim. Geterotsikl. Soedin., No. 7, 955 (1996).
A. T. Soldatenkov, I. A. Bekro, Zh. A. Mamyrbekova, S. A. Soldatova, and A. I. Chernyshev, Khim. Geterotsikl. Soedin., No. 5, 653 (1997).
H. H. Wasserman and W. R. Waterfield, Chem. and Ind., No. 8, 1220 (1961).
Kh. A. R. Alarkon, A. T. Soldatenkov, S. A. Soldatova, A. U. Samal'oa, Kh. U. Obando, and N. S. Prostakov, Khim. Geterotsikl. Soedin., No. 9, 1233 (1993).
C. J. Brown, J. Am. Chem. Soc.,75, 3265 (1953).
P. Gantzel and K. Trueblood, Acta Crystallogr.,B18, 958 (1965).
M. Sheehan and D. J. Cram, J. Am. Chem. Soc.,91, 3533 (1969).
L. N. Kuleshova, V. N. Khrustalev, Yu. T. Struchkov, A. T. Soldatenkov, A. T. Mamyrbekova, I. A. Bekro, S. A. Soldatova, and V. N. Gryshev, Zh. Strukt. Khim.,37, 957 (1996).
F. H. Allen, O. Kennard, and D. S. Watson, J. Chem. Soc., Perkin Trans. II, No. 12, 1 (1987).
R. Taylor, O. Kennard, and W. Versichel, J. Am. Chem. Soc.,106, 244 (1984).
I. L. Knunyants (ed.), Chemical Encyclopedia [in Russian], Soviet Encyclopedia, Moscow (1990), p. 286.
W. Robinson and G. M. Sheldrick, in: Crystallographic Computing. Techniques and New Technologies, N. W. Isaacs and M. R. Taylor (eds.), Oxford University Press, Oxford (1988), p. 366.
L. Y. Ying and W. F. Gorham, J. Org. Chem.,34, 1366 (1969).
H. Malmberg and M. Nilsson, Tetrahedron,42, 3981 (1986).
Additional information
For communication 9 see [1]. This report is also communication [5] in the series “Synthesis, Structure, and Biological Activity of [2.2]Paracyclophanes” (for communication 4 see [2]).
Russian University of National Friendship, Moscow 117198. A. N. Nesmeyanov Institute of Organoelemental Compounds, Russian Academy of Sciences, Moscow 117813. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 793–800, June, 1997.
Rights and permissions
About this article
Cite this article
Kryvenko, L.I., Soldatenkov, A.T., Zvolinskii, O.V. et al. Indolopyridines with a bridging heteroatom. Chem Heterocycl Compd 33, 691–697 (1997). https://doi.org/10.1007/BF02291801
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF02291801