The intereaction of 4,5-diformyl-2,3,6,7,8,10-hexahydroacridine-8a(1h)-carbonitrile with n-nucleophiles

Authors

  • E. V. Zalizna Ukrainian State University of Chemical Technology, Ukraine
  • T. P. Polishuk Ukrainian State University of Chemical Technology, Ukraine
  • S. A. Varenichenko Ukrainian State University of Chemical Technology, Ukraine
  • O. K. Farat Lomonosov Moscow State University, Russian Federation
  • V. I. Markov Ukrainian State University of Chemical Technology, Ukraine

DOI:

https://doi.org/10.24959/ophcj.16.888

Keywords:

hydroacridines, Shiff's bases, macrocycles

Abstract

Schiff bases are of practical interest as initial materials both for the combinatorial synthesis for libraries of compounds, and for preparation of complexes with metals; thus, currently the intensity of research in this direction is increasing. The possibilities of practical use of complex compounds with organic ligands are quite broad varying from effective catalysts of various chemical processes to molecular sensors. While studying formylation of 5,6,7,8-tetrahydro-1H-spiro[cyclohexane-1,2-quinazolin]-4’(3’H)-one a new domino reaction, which makes it possible to obtain tricyclic acridine systems, has been carried out. In spite of the reduced electrophilicity of the aldehyde groups in 4,5-diformyl-2,3,6,7,8,10-hexahydroacridine-8а(1H)-carbonitrile the latter is shown to react with various amines in benzene with azeotropic removal of water using p-TsOH as a catalyst, and with hydroxylamine hydrochloride in i-PrOH. New Schiff bases and oxime obtained are of potential interest as ligands for formation of chelate complexes. The reaction of dialdehyde with N2H4×H2O instead of the expected hydrazone resulted in obtaining a macrocyclic compound – a derivative of hexaazacyclooctadecine. The structure of the compounds obtained corresponds to the data of 1H NMR-spectroscopy, mass spectrometry and elemental analysis. The preliminary studies have shown that azomethines – 4,5-phenyl(cyclohexcyl)iminomethyl-2,3,6,7,8,10-hexahydroacridine8а(1H)-carbonitrile create complexes with copper and nickel ions.

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Published

2016-09-19

How to Cite

(1)
Zalizna, E. V.; Polishuk, T. P.; Varenichenko, S. A.; Farat, O. K.; Markov, V. I. The Intereaction of 4,5-Diformyl-2,3,6,7,8,10-Hexahydroacridine-8a(1h)-Carbonitrile With N-Nucleophiles. J. Org. Pharm. Chem. 2016, 14, 38-42.

Issue

Vol. 14 No. 3(55) (2016)

Section

Original Researches

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Copyright (c) 2016 National University of Pharmacy

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