Abstract
The 9-(β-pyridylmethylene)-4-azafluorene was obtained as the mixture of the Z- and E-isomers. Condensation of 4-azafluorene with methiodides of 3-formylpyridine afforded the methiodides of these isomers which were isolated in discrete form. Their configuration was established. It was established using the example of the reduction of the methiodide of the Z-isomer by sodium borohydride that the β-pyridinium portion of this quaternary salt is completely reduced to the piperidyl.
Similar content being viewed by others
References
N. S. Prostakov, N. S. Fedorov, and A. T. Soldatenkov, Zh. Org. Khim.,16, 2373 (1980).
L. A. Murugova, M. A. Galiullin, I. R. Kordova, V. P. Zvolinskii, A. T. Soldatenkov, P. K. Radzhan, and N. S. Prostakov, Zh. Org. Khim.,7, 2209 (1981).
N. M. Kolyadina, L. A. Murugova, A. T. Soldatenkov, A. A. Ustenko, and N. S. Prostakov, Khim. Geterotsikl. Soedin., No. 11, 1513 (1992).
N. M. Kolyadina, A. T. Soldatenkov, M. A. Ryashentseva, and N. S. Prostakov, Izv. R. Akad. Nauk Ser. Khim., No. 1, 180 (1996).
R. E. Lyle and P. S. Anderson, Advances in Heterocyclic Chemistry, Vol. 6, Acad. Press, New York (1966), p. 45.
M. Ferles and J. Pliml, Advances in Heterocyclic Chemistry, Vol. 12, Acad. Press, New York (1970), p. 59.
Additional information
Russian University of the Friendship of Peoples, Moscow 117923. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1243–1246, September, 1998.
Rights and permissions
About this article
Cite this article
Kolyadina, N.M., Soldatenkov, A.T., Soro, S. et al. 9-(β-pyridylmethylene)-4-azafluorene synthesis of the Z- and E-isomers of its methiodides and reduction of the Z-isomer. Chem Heterocycl Compd 34, 1066–1069 (1998). https://doi.org/10.1007/BF02251552
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF02251552