Synthesis of 2-aryloxy-4,6-bis(4-carboxyphenyl)-sym-triazines and their chlorides

The peculiarities of the reaction of some substituted (in the benzene ring) 2,4-dichloro-6-aryloxy-sym-triazines with toluene under the conditions of the Friedel-Crafts reaction were investigated. Methods for the synthesis of 2-arloxy-4,6-bis(4-carboxyphenyl)-sym-triazines and their chlorides were developed. Cleavage of the ether bond to give a dihydro-sym-triazine structure occurs in the case of 2,4-dichloro-6-benzyloxy-sym-triazine.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1125–1129, August, 1983     

Synthesis and structures of 4,6-disubstituted 2-(5-methyl-1,2,4-oxadiazol-3-yl)-1,3,5-triazines

New 1,2,4-oxadiazolyl-1,3,5-triazines were synthesized from amidoximes derived from sym-triazine mononitriles. The structure of one of the resulting compounds was studied in detail by X-ray diffraction. __________ Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1845–1850, August, 2005.     

<Emphasis Type="Italic">sym</Emphasis>-triazines. 8. Synthesis and some reactions of 4,6-disubstituted 2-(1H-pyrrolyl)-1,3,5-triazines

We have studied the reaction of 2,5-dimethoxytetrahydrofuran with 4,6-disubstituted 2-amino-1,3,5-triazines with the aim of obtaining novel coupled polyheterocyclic systems with potential bioactivity. Reaction conditions were optimized. A series of novel 4,6-disubstituted 2-(1H-1-pyrrolyl)-sym-triazines was obtained. It was found that the product yields depended on the nature of the substituent in the 4 and 6 positions of the triazine ring and on the reaction conditions. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 440–451, March, 2008.     

Chlorotropic rearrangement of 3,5-dichloro-3-cyano-4-methylpyridine-2,6-(1H)-dione in the medium of polar solvents. Synthesis of 5-chloro-3-cyano-6-hydroxy-4-methylpyridin-2-one

Isomeric conversion of 3,5-dichloro-3-cyano-4-methylpyridine-2,6(1H)-dione to 5,5-dichloro-3-cyano-4-methylpyridine-2,6(1H)-dione in polar solvents was shown. A new method for the synthesis of 5-chloro-3-cyano-6-hydroxy-4-methylpyridin-2-one was proposed.All-Russian Scientific Research Institute of Biological Plant Protection, Krasnodar 350039, Russia. Kuban' State Agrarian University, Krasnodar 350044, Russia. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1641–1644, December, 1999.     

Reaction of cyanuryl chloride and some of its monosubstituted derivatives with toluene

The Friedel-Crafts reaction of cyanuryl chloride and some of its monosubstituted derivatives with toluene was studied. It is shown that the type and character of the substituent in the 6 position of the starting derivatives of cyanuryl chloride have a strong effect on the course of the reaction. The reaction of cyanuryl chloride and its phenyl and phenoxy derivatives with toluene leads smoothly to the formation of 2,4,6-tris- and 2-substituted 4,6-bis(4-methylphenyl)-sym-triazines. 4,6-Bis(4-methylphenyl)2-oxo-2,3-dihydro-sym-triazine is formed in the case of alkoxy-substituted cyanuryl chlorides. In the case of amino derivatives of cyanuryl chloride the reaction with toluene takes place only upon prolonged refluxing and gives the final products in low yields.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 558–561, April, 1979.     

Synthesis of some esters and amides of 2-substituted 4,6-bis(p-carboxyphenoxy)-sym-triazine

A number of corresponding esters and amides were obtained by the reaction of the chlorides of 2-substituted 4,6-bis(p-carboxyphenoxy)-sym-triazines (CPT) with ethanol and some primary amines in the presence of a hydrogen chloride acceptor. It was observed that hydrazine and hydrazine hydrate have a cleavage effect on the C-O bond of chloride of CPT in the 4 and 6 positions even at 0 °C. Dihydrazides of CPT were synthesized at –40 °C.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1406–1411, October, 1981.     

Synthesis,structures, and properties of bis(4,6-disubstituted 1,3,5-triazin-2-yl) ethers

Reactions of (4,6-disubstituted 1,3,5-triazin-2-yl)trimethylammonium chlorides with glycine sodium salt in the presence of Et₃N afforded bis(triazin-2-yl) ethers instead of the expected triazinylaminoacetic acids. The structures of the resulting compounds were established by the independent synthesis, spectroscopic data, and X-ray diffraction analysis.