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

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(1Н)-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 N 2 H 4 ×H 2 O 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 1 H 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-hexahydroacridine-8а(1Н)-carbonitrile create complexes with copper and nickel ions.

Synthesis of new Schiff bases based on formyl derivatives of xanthenes

“…Previously, in the course of studying the rearrangement of geminal azines under the action of a formylating agent, we prepared 4,5-diformyl-2,3,6,7,8,10-hexahydroacridine-8a-(1H) -carbonitrile [11] and 2-methyl-4-oxo-1,5-diazaspiro [5.5]undec-2-ene-3-carbaldehyde [12], in which the aldehyde group was coupled with an electron-donor substituent. Despite the reduced reactivity of the aldehyde group, Schiff bases were obtained by the reaction with various amines [13,14].…”

“…To conclude, new Schiff bases have been synthesized based on formyl derivatives of xanthenes in this work. The structures of these compounds have been fully characterized by FT-IR, 1 H NMR, 13 Experimental The 1 H NMR and 13 C NMR spectra were recorded using a Bruker Avance II 400 instrument (400.13 MHz and 100.62 MHz for 1 H and 13 C, respectively) in DMSO-d 6 or DMSOd 6 /CF 3 CO 2 D with Me 4 Si as internal standard. The FTIR spectra were recorded in KBr pellets using a Spectrum one (PerkinElmer) FT-IR spectrometer.…”