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

E. V. Zalizna, T. P. Polishuk, S. A. Varenichenko, O. K. Farat, V. I. Markov

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.

Keywords


hydroacridines, Shiff's bases, macrocycles

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References


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

Abbreviated key title: Ž. org. farm. hìm.

ISSN 2518-1548 (Online), ISSN 2308-8303 (Print)