Synthesis and Properties of Macrocyclic Compounds With Fragment of Methylindandone

Abstract

The present communication is a continuation of the systematic studies of the authors in the field of synthesis and studying the properties of macroheterocyclic compounds, as large as possible structural modifications allow currently to synthesize macroheterocyclic compounds, differing in composition, the nature of their constituent heteroatoms and make this class of compounds promising from the point of view of directed synthesis to obtain materials with valuable practical properties. Condensation products and macroheterocyclic compounds of a symmetrical structure are synthesized by the interaction of diimine 2-methylindandione-1,3 with 2,4-diaminobenzenesulfonic acid and 3,5-diamino-1,2,4-thiadiazole in a molar ratio of 2:1. Condensation products constitute a powdery substance with different shades of red color, soluble in water and organic solvents of different nature. Macroheterocyclic compounds were synthesized with two ways. The first method is cyclization of compounds of structure 2:1 in a symmetric structure, and the second in a molar ratio of the starting materials. A purification was performed by column chromatography on alumina of II degree of activity by Brockmann eluent acetone - chloroform, 1:1 by volume. An identification of the synthesis products was performed by thin-layer chromatography on plates Silufol UV-254 (eluent – acetone - chloroform, 1:1 by volume). The compounds were characterized by data of IR, electronic and 1H NMR spectroscopy. Electronic absorption spectra were measured on instrument Hitachi U-2010 in quartz cuvettes at 20 °C. IR spectra were obtained on the device Avatar 360 FT-IR ESP in KBr. 1H NMR spectra of solutions of samples in acetone – D6 were recorded on device "AMD Brucker 500" with an internal standard of TMS. The data of elemental analysis obtained on the instrument CHNS-O Analyzer FlashEA 1112 Series. A hypsochromic shift of the absorption bands was observed upon closure in a cycle. The widened absorption bands in the visible part of the electron spectrum indicate that the molecules of synthesized compounds have a flat structure and the absorption due to individual fragments, which are part of molecules and single-chain pairing of the synthesized structures.Forcitation:Berezina G.R., Nikolaeva K.A. Synthesis and properties of macrocyclic compounds with fragment of methylindandone. Izv. Vyssh. Uchebn. Zaved. Khim. Khim. Tekhnol. 2018. V. 61. N 6. P. 29-34