Synthesis and alkylation of 2-mercapto-4-quinazolone and the fungicidal activities of the compounds obtained

A convenient method of obtaining 2-mercapto-4-quinazolone has been developed and the alkylation of its ambidentate anions has been studied. It has been found that they exhibit a dual reactivity in alkylation reactions. It has been shown that alkylated 2-mercapto-4-quinazolones possess a moderate fungicidal activity.     

Kinetic investigation of the alkylation of salts of 2,5-dimercapto-1,3,4-thiadiazole

A kinetic investigation has been carried out, using electronic absorption spectra, of the alkylation with benzyl chloride of the dihydrazine, monohydrazine, and the disodium salts of 2,5-dimercapto-1,3,4-thiadiazole, and also of the hydrazine and sodium salts of 5-benzylthio-2-mercapto-1,3,4-thiadiazole. The rates orders and constants were established for the benzylation reaction and it was noted that the reaction rate depends on the cation of these salts and the degree of substitution of the 2,5-dimercapto-1,3,4-thiadiazole.Institute of Chemistry, Vilnius LT-2600, Lithuania; Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 972–977, July, 2000.     

Studies on triacetic acid lactone-annulated heterocycles: synthesis of 3-aryloxyacetyl-6-methyl-2,3-dihydrothieno[3,2-c]pyran-4-ones by tandem cyclization

The hitherto unreported 3-aryloxyacetyl-6-methyl-2,3-dihydrothieno[3,2-c]pyran-4-ones were synthesized in 62–71% yield by the sulfoxide rearrangement of 4-(4′-aryloxybut-2′-ynylthio)-6-methyl-2-pyrone. The substrates were synthesized by phase-transfer-catalysed alkylation of the hitherto unreported 4-mercapto-6-methylpyran-2-one.     

Alkylation of benzene with 4-methylcyclohexanol in the presence of sulfuric acid

Alkylation of benzene with 4-methylcyclohexanol in the presence of methylcyclohexane and 96, 88, and 80% H₂SO₄ has been studied. It was established that depending on the solubility of the starting components in sulfuric acid, alkylation occurs in the inorganic phase or on the interface between the organic and inorganic phases. The yield and composition of the catalysate are determined to a significant degree by the extent of the alkylation process and intramolecular hydride transfers.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 1, pp. 121–125, January, 1990.     

Structure and reactivity of 2-methyl-9-hydroxy-4H-pyrido[1,2-a]pyrimidin-4-one

It has been shown that the alkylation of 2-methyl-9-hydroxy-4H-pyrido[1,2-a]pyrimidin-4-one takes place at the oxygen atom, but electrophilic substitution takes place mainly at position 8 of the molecule (the ortho position relative to the hydroxy group).Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1660–1666, December, 1992.     

Synthesis and reactions of some derivatives of 1,2-dihydrothiazolo [3,2-a]pyridinium salts

The condensation of 2-mercaptopyridine, 2-mercapto-4-methylpyridine, and 2-mercapto-6-methylpyridine with -bromoacetaldehyde and its diethyl acetal has given cyclic products (3-hydroxy- and 3-ethoxy-2,3-thiazolo[3,2-a]pyridinium salts), from which cyanine dyes have been synthesized.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1254–1257, September, 1973.     

Composition of the products and kinetics of the isopropylation of 1,2,3,4-tetrahydroquinoline in sulfuric acid

The kinetics of the alkylation of 1,2,3,4-tetrahydroquinoline with isopropyl alcohol in 90% sulfuric acid at 60 °C were studied. It was established that the rate of alkylation in the 5 position is higher than for the corresponding position in the acyclic analog N,2-dimethylaniline; this was ascribed to the Mills—Nixon dynamic effect.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 506–509, April, 1984.     

Methanol conversion on high-silica zeolites with different alumosilicate modules and prepared in different ways

High-silica zeolites in the H-form that differ in the SiO₂/Al₂O₃ ratio and the method of synthesis, have similar acidity spectra but different distributions of the acidic centers with respect to strength. A symbatic change in the concentration of the strongly acidic centers and of the degree of conversion of methanol has been observed, as well as a change in selectivity for C₂–C₄ aliphatic and aromatic hydrocarbons. It has been established that the stages of dehydration of methanol and dimethyl ether, and of aromatization and alkylation occur on strongly acidic centers of high-silica zeolites, and polymerization reactions on weakly acidic centers.Translated from Teoreticheskaya i Éksperimental'naya Khimiya, Vol. 23, No. 3, pp. 380–383, May–June, 1987.     

4-Hydroxy-2-quinolones. 32. Synthesis and antithyroid activity of thio analogs of 1H-2-oxo-3-(2-Benzimidazolyl)-4-hydroxyquinoline

We propose preparative synthesis methods for 2-thio-4-hydroxy-, 2-oxo-4-mercapto-, and 2-thio-4-mercapto-1H-3-(2-benzimidazolyl)quinolines. We have studied the antithyroid activity of the synthesized compounds.Ukraine Pharmaceutical Academy, Kharkhov 310002. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 692–696, May, 1997.     

Condensed heterocycles containing a thiazole ring. 19. Naphthothiazolopyridinium(quinolinium) salts

It is shown that the salts of condensed naphthothiazoloazines are formed by the interaction of 2,3, dichloro-1,4-naphthoquinone with 2-mercaptopyridine or 2-mercapto-4-R-quinoline.For Communication 18, see [1].Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1406–1408, October, 1990.     

Halogenation of some substituted 3-allyl-2-mercapto-3,4-dihydrothieno[2,3-d]pyrimidines

The bromination and iodination of substituted 3-allyl-2-mercapto-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidines have been studied.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1289–1290, September, 1973.     

Reductive alkylation ofE. coli L-asparaginase

Alkylasparaginases have been obtained with the far-reaching modification of 1–10 lysine residues per subunit of the enzyme. It has been established that alkylation does not affect the stability of the enzyme, and the change in the pH optimum of the catalytic action is due to the chemical nature of the alkyl substituent.Institute of Organic Synthesis, Academy of Sciences of the Latvian SSR, Riga. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 232–235, March–April, 1980.     

Condensed heterocycles. 44. Synthesis and structure of imines of 2-mercaptobenzo[b]-furan-3-carbaldehydes and 3-mercaptobenzo[b]furan-2-carbaldehydes and their derivatives

A number of isomeric mercapto aldimines of benzo[b]furan have been obtained and their structure and properties have been studied in comparison with their benzo[b]-thiophene analogs. It has been shown that the nature of the heterocycle has no substantial influence on the structure and properties of these compounds, in contrast to the initial mercapto and hydroseleno aldehydes. It has been observed that the 2-mercapto or 2-methylthio(methylseleno) groups in benzo[b]furan-3-carbaldehydes are readily replaced by an amino group, while they are not replaced in the isomeric 3-mercapto- and 3-methylthio(methylseleno)benzo[b]furan-2-cabaldehydes.For communication 43, see [1].Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 598–602, May, 1985.     

Preparation of spiroaziridinefluorene,spiroindoxyl-fluorene,and Β-aminopropionic acid ester with a 4-azafluorene fragment

It has been established that the reaction of 9-(p-methoxyphenylimino)fluorene with dichlorocarbene (conditions of phase-transfer catalysis) proceeds in two directions — the formation of spiroaziridinefluorene and of spiroindoxylfluorene, the structure of which has been demonstrated. Opening of the aziridine ring of spiroaziridinefluorene has been accomplished. From the analagous azamethine, 4-aza-fluorene, an ester of N-substituted -aminopropionic acid with a 4-azafluorene fragment was obtained by alkylation of its dianion with methyl chloroacetate.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 895–897, July, 1986.     

Alkylation of 2-, 4-, and 8-trialkylsiloxyquinolines by methyl iodide

Trimethyl- and triethylsilyl ethers of 2-, 4-, and 8-hydroxyquinolines have been prepared. The alkylation of these siloxyquinolines by methyl iodide has been studied. In the case of 4-trimethylsiloxyquinoldine, it has been established that both N- and O-alkylation products are formed.Latvian Institute of Organic Chemistry, Riga LV-1006. Translated from Khimiya Geteortsiklicheskikh Soedinenii, No. 9, pp. 1225–1231, September, 1994. Original article submitted September 28, 1994.     

Synthesis and Antiviral Activity of 1-{[2-(Phenoxy)ethoxy]methyl}uracil Derivatives

The synthesis of novel 1-{[2-(phenoxy)ethoxy]methyl}uracil derivatives with different substituents in positions and 6 of the pyrimidine ring has been carried out. It has been shown that the alkylation of trimethylsilyl derivatives of uracil with 2-(4-chlorophenoxy)- and 2-(4-methylphenoxy)ethoxymethyl chloride under Hilbert-Johnson reaction conditions gives N₍₁₎-substitution products. It was found that the 1-{ [2-(phenoxy)ethoxy]methyl}uracil derivatives show viral inhibition properties relative to human immunodeficiency type 1 virus in vitro. The most active compounds are 5-bromo-6-methyluracil derivatives which suppress viral reproduction by 50% at 7.2 and 7.8 micromolar concentrations.__________Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 726–731, May, 2005.     

Synthesis and some transformations of sulfides of the thiophene series

Some 2-substituted 4-keto-2,3-dihydrothieno[3,2-e]-1,3-thiazines were obtained by condensation of 2-mercapto-5-ethylthiophene-3-carboxamide with aldehydes and ketones in the presence of gaseous HCl.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 909–910, July, 1972.     

Alkylation of 3-cyano-4-methoxymethyl-6-methyl-2(1h)-pyridone by active halomethylene compounds. The molecular structure of 3-amino-2-benzoyl-4-methoxymethyl-6-methylfuro[2,3-<Emphasis Type="Italic">b</Emphasis>]pyridine

The alkylation of 3-cyano-4-methoxymethyl-6-methyl-2(1H)-pyridone by active halomethylene compounds has been studied. It was shown that the reaction of the pyridone with methyl- and ethylchloroacetates and phenacyl and p-bromophenacyl bromides occurs to give N- and O-structural isomers. Only the N-derivatives are separated from the reaction mixture when the pyridone is alkylated with iodoacetamide. It was found that 2-aroylmethyl-3-cyano-4-methoxymethyl-6-methylpyridines cyclize in the presence of KOH to 3-amino-2-aroyl-4-methoxymethyl-6-methylfuro[2,3-b]pyridines. The molecular structure of 3-amino-2-benzoyl-4-methoxymethyl-6-methylfuro[2,3-b]pyridine has been studied using an X-ray analytical method.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1670–1682, November, 2004.     

Synthesis of the acetate of octadeca-trans-2,cis-13-dien-1-ol,a component of the sex pheromones of Synanthedon tipuliformis and Zeuzera pyrina

A new synthesis of the acetate of octadeca-trans-2,cis-13-dien-1-ol based on the alkylation of propargyl alcohol with pentadec-cis-10-enyl bromide, obtained from the readily accessible decamethylene bromohydrin, has been effected.All-Union Scientific-Research Institute of Biological Methods of Plant Protection, Kishinev. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 264–266, March–April, 1989.     

Synthesis and properties of 4-(3-aminothieno-[2,3-b]pyridin-2-yl)coumarins

Substituted 4-[(3-cyanopyridin-2-yl)thiomethyl]coumarins have been synthesized by the alkylation of 2-mercapto-4,6-dimethylnicotinonitrile with 4-chloromethylcoumarins. Substituted 4-(3-amino-thieno[2,3-b]pyridin-2-yl)coumarins have been obtained by a subsequent intramolecular condensation of the methylene and cyano groups. 6H-Chromeno[4,3-d]thieno[3,2-b:5,4-b']dipyridin-6-ones were isolated as a result of the interaction of these compounds with aldehydes, and their aminomethyl derivatives were synthesized.