Abstract
The reaction of 1-hydroxy-1-methyl-1H-3-(1-oxo-6-tert-butylisoindolin-3-ylidenemethyl)-5-tert-butylisoindole, which is the product from the condensation of potassium 4-tert-butylphthalimide and malonic acid, with phthalonitrile or 3-iminophthalimide leads to the formation of a mixture of the tert-butyl-substituted mono-, di-, and triaza analogs of zinc tetrabenzoporphin. The mixture was separated by chromatography on aluminum oxide. The zinc complex of di(4-tert-butylbenzo)di-benzodiazaporphin is demetallated by the action of HCl in acetic acid. The characteristics of the synthesized compounds are given.
Similar content being viewed by others
Literature Cited
Y. H. Helberger, Annalen, 529, 205 (1937).
Y. H. Helberger and A. Rebay, Annalen, 531, 279 (1937).
P. A. Barrett, R. P. Linstead, and G. A. Tuey, J. Chem. Soc., No. 11, 1809 (1939).
T. F. Kachura, V. A. Mashenkov, K. N. Solov'ev, and S. F. Shkirman, Izv. Akad. Nauk BSSR, No. 1, 65 (1969).
S. W. Oliver and T. D. Smith, J. Chem. Soc., Perkin 2, No. 11, 1579 (1987).
K. H. Solov'ev, V. A. Mashenkov, A. T. Gradyushko, and A. E. Turkova, Zh. Prikl. Spectrosk., 13, 339 (1970).
V. N. Kopranenkov, E. A. Tarkhanova, and E. A. Luk'yanets, Zh. Org. Khim., 15, 642 (1979).
S. A. Mikhalenko, S. V. Barkanova, O. L. Lebedev, and E. A. Luk'yanets, Zh. Obshch. Khim., 41, 2735 (1971).
A. Braun and Y. Tcherniac, Berichte, 40, 2709 (1907).
Author information
Authors and Affiliations
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1385–1390, October, 1989.
Rights and permissions
About this article
Cite this article
Makarova, E.A., Kopranenkov, V.N., Shevtsov, V.K. et al. New method for synthesis of the aza analogs of tetrabenzoporphin. Chem Heterocycl Compd 25, 1159–1164 (1989). https://doi.org/10.1007/BF00470696
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/BF00470696