BGR Macroheterocyclic Compounds of Asymmetric Structure With Thiadiazol Fragments. Synthesis and Properties

Abstract

This communication is a continuation of the systematic research of the authors in the field of synthesis and study of the properties of macroheterocyclic compounds. The great potential for structural modification allows us to synthesize macroheterocyclic compounds that differ in composition and the nature of the heteroatoms that make up them and make this class of compounds promising from the point of view of the design for the preparation of substances with valuable practical properties. The interaction of N,N/-bis-(1-imino-2-phenyl-1H-indene-3-iliden)-1,4-phenylenediamine with 2,5-dimiano-1,3,4-thiadiazole and 3,5-diamino-1,2,4-thiadiazole the macroheterocyclic compounds of asymmetric structure were synthesized in the molar ratio of the initial substances. Macroheterocycles are powdered substances with different shades of red color, having melting and crystallization temperatures (investigated in the argon current), soluble in chloroform, DMF, acetone, ethanol. Purification was carried out by column chromatography on aluminum oxide of II degree of activity on Brockman (eluent acetone - chloroform, 1:9 by volume). Identification of synthesis products was performed by thin-layer chromatography on Silufol UV-254 plates (eluent – acetone - chloroform, 1:1 by volume). The obtained compounds were characterized by infrared and electron spectroscopy. The electronic absorption spectra were measured on a Hitachi U-2010 instrument in quartz cuvettes at 20 °C. IR spectra were obtained on the Avatar 360 FT-IR ESP device in KVG. Elemental analysis data were obtained using the CHNS-O Analyzer FlashEA of 1112 Series. A bathochromic shift of the absorption bands was noted when the compound with 1,3,4-thiadiazole was closed in a cycle. The spectral characteristics indicate that the molecules of the synthesized compounds do not have a flat structure and the absorption is due to individual fragments that are part of the molecules of the synthesized structures.