I. Aleksanyan, L. Hambardzumyan
Apr 23, 2014
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Russian Journal of Organic Chemistry
Abstract
Among functionally substituted quinoline derivatives, those containing sulfur occupy a particular place due to their antitumor, analgesic, antimicrobial, and other kinds of biological activity [1]. They also exhibit good antioxidant properties and are used in anti-stress therapy [2]. Sulfur-containing compounds comprising more than one heterocyclic fragment attract increased interest as fluorophores [3] and play an important role in studying various biological systems [4]. Quinoline derivatives are also promising as fluorophores [5], antioxidants, and radioprotectors [6]. With a view to synthesize new quinoline derivatives, in the present work we examined reactions of 2-chloro-4-methylquinolines Ia–Ic with biphenyl-4,4′dithiol, 4,4′-sulfanediyldibenzenethiol, 1,3-benzothiazole-2-thiol, biphenyl-4,4′-diyldimethanethiol, (oxydibenzene-4,1-diyl)dimethanethiol, and benzene-1,4-diyldimethanethiol. Optimal reaction conditions were found. Bis-quinoline derivatives were mainly formed at different reactant ratios. The reactions ensured high yields when mixtures of 2-chloroquinolines Ia–Ic [7] with the corresponding binucleophiles at a ratio of 2 : 1 (1 : 1 in the reaction with 1,3-benzothiazole-2-thiol) were heated in boiling ethanol over a period of 3–5 h. As a result, we isolated substituted 4,4′-bis(quinolin-2ylsulfanyl)biphenyls IIa–IIc, bis[4-(quinolin-2-yl)phenyl] sulfides IIIa–IIIc, 4,4′-bis(quinolin-2-ylsulfanylmethyl)biphenyls IVa–IVc, 2,2′-[oxybis(benzene-4,1diylsulfanediyl)]bis(4-methylquinolines) Va–Vc, 1,4-bis(quinolin-2-ylsulfanyl)benzenes VIa–VIc, and ISSN 1070-4280, Russian Journal of Organic Chemistry, 2014, Vol. 50, No. 3, pp. 442–444. © Pleiades Publishing, Ltd., 2014. Original Russian Text © I.L. Aleksanyan, L.P. Hambardzumyan, 2014, published in Zhurnal Organicheskoi Khimii, 2014, Vol. 50, No. 3, pp. 421–423.