Synthesis of polynuclear heterocyclic polynitrogen systems based on cyanuric chloride and its derivatives

Abstract

Polynuclear structures containing several heterocycles of various types were synthesized by the reaction of cyanuric chloride and its mono-and dichloro derivatives with triazoles and tetrazoles in the presence of bases.In our earlier papers we demonstrated the fundamental possibility of the synthesis of noncondensed polynuclear triazole-and tetrazole-containing units by the gradual insertion of new heterocycles into the initial azole [1,2]. In a continuation of these investigations in the present work we have examined a version of the synthesis of polynuclear structures based on the molecules of cyanuric chloride (1), 2-chloro-4,6-dimethoxy-1,3,5-triazine (2), 2-chloro-4,6-dimorpholino-1,3,5-triazine (3), 2,4-dichloro-6-methoxy-1,3,5-triazine (4), and 2,4-dichloro-6-diethylamino-1,3,5-triazine (5). As known, cyanuric chloride readdily enters into reaction with various nucleophiles [3,4]. It was assumed that this compound and its derivatives would react no less vigorously with azoles, forming polynuclear structures. It is known that one of the chlorine atoms in cyanuric chloride initially reacts quite readily in substitution reactions [3,4]. Actually, the reaction of 1 mol of 5-phenyltetrazole with cyanuric chloride at 0-5°C leads to the production of 4,6-dichloro-2-(5-phenyltetrazol-1-yl)-1,3,5-triazine (6). Substitution of the other chlorine atoms already requires a somewhat higher reaction temperature. Thus, trisubstituted polynuclear azolyl-containing compounds 7a-c, based in a 1,3,5-triazine ring, are formed during the reaction of cyanuric chloride with 3 mol of tetrazole, 5-phenyltetrazole, and ethyl (tetrazole-5-yl)acetate in the form of triethylammonium salts or in the presence of sodium hydrocarbonate in a water-acetone medium at 15-25°C. As a rule the isolated compounds are high-melting substances poorly soluble in organic solvents. In order to produce polycyclic compounds with lower melting points and soluble in organic solvents methoxy and alkylamino groups were inserted into the molecule of the triazine ring. Here the monochlorotriazines 2 and 3 and the dichlorotriazines 4 and 5 were synthesized, and they were then brought into substitution reactions with azoles.

A non-dispersive infrared sensor for real-time detection of cyanogen chloride

“…For example, CNCl is used to produce cyanuric chloride and the synthesis of tetramethyl guanidine. 1,2 CNCl has the characteristics of low boiling point and volatility and usually exists as a gas. 3,4 Cyanogen in CNCl has strong coordination ability.…”