Specific Features of the Reactions of Pentaphenylantimony with Polyfunctional Heterocyclic Carboxylic Acids

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ific Features of the Reactions of Pentaphenylantimony with Polyfunctional Heterocyclic Carboxylic Acids Yu. O. Gubanovaa,*, V. V. Sharutina, O. K. Sharutinaa, and K. Yu. Petrovaa a

National Research South Ural State University, Chelyabinsk, 454080 Russia *e-mail: [email protected] Received April 21, 2020; revised April 21, 2020; accepted April 30, 2020

Abstract—Pyridine-2,6- and 2,5-dicarboxylic acids have acted as bifunctional compounds in the reactions with pentaphenylantimony, forming bis(tetraphenylantimony)pyridine-2,6- and 2,5-dicarboxylate, respectively. The interaction of pentaphenylantimony with 2-[(6-hydroxy-5-nitroso-4(3H)-oxopyrimidin-2-yl)sulfanyl]acetic acid involving carboxyl and hydroxyl groups in the pyrimidine ring has afforded 2-{[5-nitroso-4(3H)-oxo-6-(tetraphenylstiboxy)pyrimidin-2-yl]sulfanyl}tetraphenylantimony acetate. The structural features of the synthesized compounds have been established by means of X-ray diffraction analysis. Keywords: pentaphenylantimony, dephenylation, pyridinedicarboxylic acids, 2-[(6-hydroxy-5-nitroso4(3H)-oxopyrimidin-2-yl)sulfanyl]acetic acid, molecular structure

DOI: 10.1134/S1070363220090121 Derivatives of pyridine and pyrimidine are biologically active; in particular, their antitumor activity has been confirmed using various cell lines [1–8]. Aryl derivatives of antimony(V) also exhibit anticancer properties; numerous studies using human and animal cells have revealed the relationship between the structure of the aryl fragment and the compound properties [9–12]. Preparation of antimony(V) complexes with heterocyclic ligands extends the range of practically important properties of antimony derivatives. Additional coordination of the heteroatom with antimony is possible in the heterocyclic antimony derivatives [13, 14] (the formation of five-membered metallocycles has been marked in certain cases [15–18]). The derivatives of antimony(V) with polyfunctional heterocyclic ligands, for example, with biquinoline [19] and pyrimidine [20] ones have been described. We performed the reactions of pentaphenylantimony with pyridine-2,6(2,5)-dicarboxylic and 2-[(6-hydroxy5-nitroso-4(3Н)-oxopyrimidin-2-yl)sulfanyl]acetic acids and elucidated the structural features of the isolated compounds. The interaction of pentaphenylantimony with pyridine-2,6- and 2,5-dicarboxylic acids in aromatic solvents was accompanied by the substitution of the hydrogen atoms in two carboxylic groups

with the Ph 4Sb fragments, affording the binuclear compounds: bis(tetraphenylantimony) pyridine-2,6(2,5)dicarboxylates as 1 : 1 solvates with benzene (1) and 1 : 2 solvates with toluene (2) (Scheme 1). The molecules of bis(tetraphenylantimony) carboxylates differed in the antimony atoms coordination. The coordination number of one of the antimony atoms in the molecule of bis(tetraphenylantimony) pyridine-2,5-dicarboxylate 2 was increased to 6 due to the formation of an additional Sb–N coordination bond. 2-[(6-Hydroxy-5-nitroso-4(3Н)-oxopyrimidin-2-yl)sulfanyl]acetic acid reacted with pentaphenylanti