Synthesis and thermal decomposition of haloalkoxy-sym-triazines. 7. Thermal decomposition of 2-dialkylamino-4-(2-chloroethoxy)-6-methoxyamino-sym-triazines

Two 2-dialkylamino-4-(2-chloroethoxy)-6-methoxyamino-sym-triazines were synthesized. It was established that when they are heated at 120° C, the 2-chloroethoxy group undergoes rearrangement with cyclization to give 2-dialkylamino-4-oxo-8-methoxy-6, 7-dihydroimidazo [1,2-a]-sym-triazines, the structure of which was confirmed by data from the IR, PMR, and mass spectra.See [6] for Communication 6.Translated from Khimiya Geterotsilicheskikh Soedinenii, No. 8, pp. 1122–1124, August, 1981.     

Some Conversions of Thiazoline Carboxylic Acid Esters

We have carried out solvolysis of the previously described ethyl esters of 3-methyl(aryl)-4-methyl-2-thioxothiazoline-5-carboxylic acids, leading to the corresponding acids without breaking down the heterocycle. We synthesized a series of novel esters from the latter by treatment with dimethyl sulfate or reactive halides. Of these, only in the case of the ethyl ester of 3,4-dimethyl-2-thioxothiazoline-5-carboxylic acid did we obtain the hydrazinolysis product (the hydrazide), from which we synthesized novel hydrazones by treatment with aldehydes and ketones.     

Investigations into functionally substituted azines.

Reaction of 2-N-potassiocyanamino-4,6-bisisopropyl(dimethylamino)-sym-triazines with acid 1,2,2,2-tetrachloroethylamides leads to the formation of 2-N-cyano-N-(1-acylamino-2,2,2-trichloroethyl)amino-4,6-bisisopropyl(dimethylamino)-sym-triazines. Reaction with 1-hydroxy(methoxy)-2,2,2-trichloroethylamides of chloroacetic acid leads to 2-(2-imino-4-oxooxazolidin-1-yl)-4,6-bis(dimethylamino)-sym-triazine and its 1-methoxy-2,2,2-trichloroethyl derivative substituted at the position 3 of the oxazolidine ring.     

Synthesis and modification of 4-hydroxy-2-methyl-3-(2-chloro-2-propenyl)quinoline

4-Hydroxy-2-methyl-3-(2-chloro-2-propenyl)quinoline was prepared by O-allylation of 4-hydroxy-2-methylquinoline followed by the Claisen rearrangement of the 2-methyl-4-(2-chloro-2-propenyloxy)quinoline obtained. Chemical modifications of 4-hydroxy-2-methyl-3-(2-chloro-2-propenyl)quinoline resulted in the synthesis of 4-amino-2-methyl-3-(2-methyl-3-indolyl)quinoline.     

Synthesis of 4-Hydroxy- and 4-Amino-2-Methyl-3-(2-Methylindol-3-Yl)methylquinolines and Their 6- and 8-Substituted Derivatives

A method has been developed for the synthesis of substituted 4-hydroxy- and 4-amino-2-methyl-3-(2-methylindol-3-yl)methylquinolines by treating the corresponding 4-hydroxy(chloro)-2-methyl-3-(3-oxobutyl)quinolines with phenylhydrazine hydrochloride. It was found that nucleophilic substitution occurred in the case of the 4-chloroquinolines together with subsequent rearrangement to give the 4-amino derivatives. The thiosemicarbazones of the corresponding 4-hydroxy-2-methyl-3-(3-oxobutyl)quinolines were also obtained.__________Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 554–557, April, 2005.     

Synthesis of 3,4‐Dialkyl‐5‐(1‐oxo‐ethyl)‐3H‐thiazole‐2‐thiones Derivatives and Their Pesticidal Activity

By interaction of N‐methyl(ethyl)‐dithiocarbamate sodium salt with 3‐chloro‐pentane‐2,4‐dion the 1‐(3‐alkyl‐4‐methyl‐2‐thioxo‐2,3‐dihydro‐thiazol‐5‐yl)‐ethanones 1 , 2 and corresponding oximes 7 , 8 were synthesized. On the basis of the mentioned compounds hydrazono ( 3 , 4 ), ureayl and thioureayl ( 5 , 6 ) derivatives, substituted oximes ( 9 , 10 ) and azinyl oximes ( 11 , 12 ) were obtained. The structures of synthesized compounds were confirmed by proton nuclear magnetic resonance spectroscopy and elemental analysis. The pesticidal activities of synthesized compounds were studied. Some of the synthesized compounds simultaneously have shown growth stimulant and fungicidal activity.     

Effect of Different Substituents on Amine-imine Tautomerism of 2-Amino-4-methylthiazole Derivatives

We have used ¹H NMR to study the amine-imine tautomerism of some esters and amides of 2-N-labeled 4-methylthiazole-5-carboxylic acids and 5-carbamic acids. We have shown that the nature of the substituents of the 2-NHR¹, 5-COR², or 5-NHCOR² groups affects that position of the tautomeric equilibrium. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1240–1243, August, 2005.     

Investigations in the area of functionally substituted azines. Synthesis and thermolysis of chlorethoxypyrimidines

The 2-amino-4-(2-chlorethoxy)-6-methyl- and 2-(2-chlorethoxy)-4-methoxy-6-methylpyrimidines were synthesized. Depending on the position of the chlorethoxy group in the ring, their therniolysis results in the formation of the oxazolopyrimidinium chloride or the N₍₁₎-(2-chlorethyl) derivative.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 237–239, February, 1996.     

Synthesis and thermal decomposition of haloalkoxy-sym-triazines. 6. Synthesis and thermolysis of 2-(2-chloroethoxy)-4-N-methyl-N-cyanoamino-6-dialkylamino-syn-triazines

2-(2-Chloroethoxy)-4-N-methyl-N-cyanoamino-6-dialkylamino-sym-triazines were synthesized. It was established that thermolysis of the indicated compounds in xylene is accompanied by dechloroalkylation; however, it takes place at the site of both the dialkylamino and alkylcyanoamino groups to give a mixture of two imidazo-sym-triazines. The structures of the latter were confirmed by data from the IR, PMR, and mass spectra.See [4] for Communication 5.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1558–1560, November, 1980.     

Synthesis and thermal decomposition of halogenoalkoxy-, halogenoalkylthio-, and halogenoalkoxyamino-sym-triazines 13. Synthesis and thermolysis of 4,6-disubstituted 2-(2-chloroethoxy)- and 2-(2-chloroethylamino)-sym-triazines

4-Amino-, 4-methoxy-, 4-methylthio-, 4-alkylamina-, and 4-dialkylamino-6-alkyl(dialkyl)amino-2-(2-chloro-ethoxy)-sym-triazines and the corresponding 2-(2-chloroethylamino)-sym-triazines were obtained. Their cyclization led to the sym-triazinium chlorides or imidazo-sym-triazines.For Communication 12, see [1].Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 228–230, February, 1992.