Synthesis and Properties of sym-Triazine Derivatives. 18. Synthesis of N-Substituted 2,4-Diamino-6-(benzothiazolyl-2-thiomethyl)-sym-triazines

The condensation of methyl benzothiazolyl-2-thioacetate with N-substituted biguanides in the presence of sodium methylate gave 2-amino-4-(RR'-amino)-6-(benzothiazolyl-2-thiomethyl)-sym-triazines. In a number of cases the 1,1-disubstituted 5-(benzothiazolyl-2-thioacetyl)biguanides could also be separated and these could be cyclized by refluxing in DMF to the corresponding substituted sym-triazines described. The latter type of compound was also synthesized by treating 2-amino-4-trichloromethyl-6-(benzothiazolyl-2-thiomethyl)-sym-triazine with primary and secondary aliphatic and heterocyclic amines or by the reaction of N-substituted 2,4-diamino-6-chloromethyl-sym-triazines with 2-mercaptobenzothiazole.     

Synthesis and properties ofsym-triazene derivatives 13. Synthesis of 6-substituted 2,4-dialkyl(aryl)thio-sym-triazenes from imino esters of carboxylic acids

6-Substituted 2,4-dialkyl(aryl)thio-sym-triazenes are synthesized by condensation of imino esters of carboxylic acids with thiocyanates.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1125-1128, August, 1994.For paper 12, see [1].     

sym-Triazine Derivatives. 2. Synthesis, Properties, and Structure of 2-Oxo-1,2-dihydro-sym-triazines

Previously unreported 2-oxo-1,2-dihydro-sym-triazines have been prepared and their alkylation reactions have been studied. It was found that, independently of the structure and nature of the substituent in positions 4 and 6 of the triazine ring or the structure of the alkyl halide used, the reaction occurs regioselectively at the oxygen atom. The stereostructure of the 2-oxo-1,2-dihydro-sym-triazines was investigated by X-ray analysis and it was shown that they exist as dimers in the crystalline state.     

Synthesis and thermal rearrangement of 2-(2-chloroethoxy)-4,6-disubstituted <Emphasis Type="Italic">sym</Emphasis>-triazines

On thermolysis of 4-methoxy- and 4-alkylamino-2-(2-chloroethoxy)-6-morpholino(piperidino)-sym-triazines, the corresponding oxazolo- or imidazo-sym-triazinones are formed by elimination of methyl chloride or hydrogen chloride, and 4,6-disubstituted 3-(2-chloroethyl)-sym-triazin-2-ones are formed from 4,6-dimorpholino(dipiperidino) derivatives.     

Derivatives of sym-Triazine. 3. Synthesis and Some Conversions of Monoazides of the Triazine Series

A convenient preparative route has been developed for the synthesis of 2-azido-4-R-6-R'-sym-triazines, which are promising synthons in organic synthesis. A series of 2-(1-triazolyl)-sym-triazine derivatives has been synthesized for the first time from the obtained azides and acetylacetone or acetoacetic ester.     

Synthesis and properties of derivatives ofsym-triazine. 15. Synthesis of amine derivatives ofsym-triazine that contain indole groups

By the cyclocondensation of imino esters of acids of the indole series with N-acylguanidines, 2-amino-4,6-disubstituted sym-triazine are obtained that contain indole groups. The reaction of N-(indolyl-3-imidolyl)-guanidine with esters of carboxylic acids leads to 2-amino-4-(3-indolyl)-6-substituted sym-triazines. Indolyl-containing N-subsitituted 2,4-diamino-sym-trizines are synthesized by the reaction of imino esters of indole acids with biguanides. Similar products are also formed when 2-amino-4-trichloromethyl-sym-triazines that contain indole substituents react with dimethylamine, morpholine, or furfurylamine.I. M. Gubkin State Petroleum and Gas Academy, Moscow, 117917. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 214–223, February, 1995. Original article submitted December 21, 1994.     

3-杂环胺基甲烯基-6-烷基(芳基)-5,6-二氢-2H-吡喃-2,4-二酮的合成及生物活性的研究

异构体;氢键;3-杂环胺基甲烯基-6-烷基(芳基)-5;6-二氢-2H-吡喃-2;4-二酮的合成及生物活性的研究     

Synthesis and properties of sym-triazine derivatives. 8. Synthesis of amino and alkoxy derivatives of sym-triazine containing fragments of a sterically-hindered phenol from 2,4-bis(trichloromethyl)-sym-triazines

The reactions of 2,4-bis(trichloromethyl)-6-substituted sym-triazines with several amino and hydroxy derivatives of 2,6-di-tert-butylphenol were studied. It is shown that, depending on the reaction conditions, one or both trichloromethyl groupings in the starting sym-triazines are replaced.See [1] for Communication 7.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 681–686, May, 1988.     

二[4-羟基-5,6-二氢-6-烷基(芳基)-2H-吡喃-2-酮-3-]烃的合成及生物活性的研究

采用5,6-二氢-6-烷基(芳基)-2H-吡喃-2,4-二酮和醛进行缩合反应,合成了二[4-羟基-5,6-二氢-6-烷基(芳基)-2H-吡喃-2-酮-3-]烃.其结构经¹HNMR和元素分析证实.对反应条件(反应温度、反应时间)进行了探讨.生物活性初步测定表明,该类化合物具有一定的杀菌和抗烟草花叶病毒的活性.     

3-aryl(alkyl)quinazoline-2,4(1<Emphasis Type="Italic">H</Emphasis>,3<Emphasis Type="Italic">H</Emphasis>)-diones and their alkyl derivatives

Two-stage reaction of methyl anthranilate with aryl(alkyl) isocyanates in keeping with the quantumchemical calculations and XRD analysis resulted in 3-aryl(alkyl)quinazoline-2,4(1H,3H)-diones that by treatment with alkyl halides, phenacyl bromides, esters and amides of chloroacetic acid were converted into the corresponding 1-alkyl derivatives.     

Synthesis and properties of sym-triazine derivatives. 3. alkoxylation of 2-alkyl-4,6-bis(trichloromethyl)-sym-triazines containing higher alkyl radicals

Nucleophilic substitution reactions of trichloromethyl groups in 2-alkyl-4,6-bis-(trichloromethyl)-sym-triazines by alkoxy radicals were studied. It was shown that in the presence of sodium alcoholates, two CCl₃ groups are replaced, and the corresponding 2,4-dialkoxy-6-alkyl-sym-triazines are formed. The products of partial replacement, 2-alkoxy-4-trichloromethyl-6-alkyl-sym-triazines, were synthesized by heating the initial sym-triazines with alcohols in the presence of tertiary amines.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1674–1677, December, 1984.     

Derivatives of <Emphasis Type="Italic">sym</Emphasis>-Triazine. 1. Synthesis and Conversions of Quaternary Methylammonium Salts of 2-Chloro-4,6-disubstituted 1,3,5-Triazines in Nucleophilic Substitution Reactions

New quaternary ammonium salts of monochloro-4,6-disubstituted 1,3,5-triazines have been obtained. These compounds are convenient synthons for the synthesis of new cyano, alkoxy, and other derivatives of sym-triazine. Some conversions of the synthesized salts have been studied. An elimination-isomerization reaction of the sym-triazine ring into a 2-oxo-1,2-dihydro-sym-triazine ring was discovered.     

Polyfunctional imidazoles: II. Synthesis and reactions with nucleophilic reagents of 1-substituted 2,4-dichloro-1<Emphasis Type="Italic">H</Emphasis>-imidazole-5-carbaldehydes

1-Alkyl(aryl)imidazolidine-2,4-diones reacted with Vilsmeier-Haack reagent affording 1-alkyl(aryl)-2,4-dichloro-1H-imidazole-5-carbaldehydes whose reactions with sodium azide, sodium alkoholates, with phenols, thiols, and secondary cycloalkylamines led to the substitution of chlorine in the position 2 of the imidazole ring. The reaction with primary amines resulted in the condensation products at the aldehyde group.     

Derivatives of sym-Triazines. 6. Some Special Features of the Addition of Substituted Acetylenes to Triazine Monoazides

The special features of the interaction of 2-azido-4-R-6-R'-sym-triazines with some acetylenic compounds have been investigated. A series of new derivatives of sym-triazine linked at position 2 with a 1,2,3-triazole ring has been synthesized.     

Novel synthesis approach and antiplatelet activity evaluation of 6-alkylamino-2,4-dialkyl(aryl)thiopyrimidines

A new and efficient procedure has been designed for the preparation of 6-alkylamino-2,4-dialkyl(aryl)thiopyrimidines. The first alkylthio group was introduced into the pyrimidine ring by S-alkylation. The introduction of the second one was successfully achieved using the diazotization-alkylthionation method to afford 2,4-dialkyl(aryl)thio-6-chloropyrimidines. Subsequent nucleophilic displacement by the corresponding amines conveniently gave a series of the target compounds. Thus, the two same or different alkylthio groups were easily introduced into the pyrimidine ring through the two different approaches. The human anti-platelet aggregation activity of the newly synthesized compounds is also described.     

Synthesis of 5-azaadenine derivatives from N-(1,2,4-triazol-5-yl)amidines

A method is proposed for the synthesis of N-substituted 5-azaadenines. The condensation of N-(1,2,4-triazol-5-yl)amidines with trichloroacetonitrile gives trichloromethyl derivatives of 1,2,4-triazolo[1,5-a]-1,3,5-triazines, which are converted by the action of primary or secondary amines into N-alkylamino- or N,N-dialkylamino-1,2,4-triazolo-[1,5-a]-1,3,5-triazines (5-azaadenines).Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 1, pp. 241–243, January, 1991.     

Synthesis of 7-Alkyl(aryl)-6-alkoxycarbonyl-5-fluoroalkyl-1,2,4-tri(tetr)azolo[1,5-a]pyrimidines

Fluorinated 3-oxo esters react with aldehydes and 3-amino-1,2,4-triazoles and 5-aminotetrazoles to give, respectively, 7-alkyl(aryl)-6-alkoxycarbonyl-5-fluoroalkyl-1,2,4-triazolo[1,5-a]pyrimidines and -tetra-zolo[1,5-a]pyrimidines. The same heterocyclic products can be obtained by reaction of 2-benzylidene-2-fluoroacyl esters with the corresponding aminoazoles.     

Synthesis of new organothiophosphorus insectoacaricides containingN-acylated amino acid fragments

Methods for the synthesis ofO-alkylS-(N-acyl-N-alkoxycarbonylalkyl)aminomethyl (methyl)thio- and -dithiophosphonates based on the reaction between alkaline-metal salts ofO-alkyl (methyl)thio- and -dithiophosphonates and N-alkoxycarbonyl-N-chloromethylglycine or --alanine esters and by treatment ofO-alkyl (methyl)dithiophosphonoates andN-acylated amino acids or their esters with paraform in the presence of HCl were developed. The compounds obtained exhibit high insectoacaricide activity and selectivity.Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1294–1301, July, 1994.     

New Approach to Synthesize Symmetrical and Unsymmetrical 6-(N-Alkyl(Aryl)Amino)- and 6-(N,N-Dialkyl(Aryl)Amino)-2,4-Bis(Alkyl(Aryl)Thio)Pyrimidines as anti-Platelet Agents

Abstract

A new and straightforward procedure has been developed for the preparation of symmetrical and unsymmetrical 6-(N-alkyl(aryl)amino)- and 6-(N,N-bisalkyl(aryl)amino)-2,4-bis(alkyl(aryl)thio)pyrimidines. The two identical or different alkylthio groups were successfully introduced into the pyrimidine ring of 4-amino-6-hydroxy-2- mercaptopyrimidine via S-alkylation with alkyl halides, and via a nucleophilic displacement with sodium alkylmercaptides, affording the key intermediate symmetrical and unsymmetrical 2,4-bis(alkyl(aryl)thio)-6-aminopyrimidines. Subsequently, N-alkylation of the 2,4-bis(alkyl(aryl)thio)-6-aminopyrimidines with alkyl halides conveniently gave the desired products. The human anti-platelet activities of all the synthesized new compounds were also evaluated.

Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.     

Synthesis and some reactions of aryl 4,5-dichloroisothiazol-3-yl ketones

By acylation of benzene, toluene, and p-xylene with 4,5-dichloroisothiazole-3-carbonyl chloride the corresponding aryl 4,5-dichloroisothiazol-3-yl ketones were obtained. By reaction of 4,5-dichloroisothiasol-3-yl 4-methylphenyl ketone with piperidine, alkyl(aryl) thiolates, sodium alcoholates, and 2,4-dinitrophenylhydrazine were synthesized 4-methylphenyl 5-piperidyl-4-chloroisothiazol-3-yl ketone, 5-alkyl(aryl)sulfanyl-4-chloroisothiazol-3-yl 4-methylphenyl ketones, 5-alkoxy-4-chloroisothiazol-3-yl 4-methylphenyl ketones, and 2,4-dinitrophenylhydrazone of the initial ketone respectively.