A general and efficient method for the synthesis of S-substituted 5-sulfanylmethyl(ethyl)-1,3,4-thiadiazol-2-amines via cyclocondensation of aryl(benzyl)sulfanylacetic and -propionic acids with thiosemicarbazide upon their heating in POCl3 was developed. Both aryl- and benzylsulfanilacetic and -propionic acids were successfully involved in this reaction to give the target thidiazolamines in high yields (63–98%).

A convenient method was developed for the combinatorial synthesis of substituted (5aS)-2-benzylthio-3-cyano-4,5a,6,7,8,10-hexahydro-5H-pyrrolo[1,2-a]thieno[3,2-e][1,4]diazepine-5,10-diones. The structure and the most probable conformation of (5aS)-2-benzylthio-3-cyano- 4,5a, 6,7,8,10-hexahydro-5H-pyrrolo[1,2-a]thieno[3,2-e][1,4] diazepine-5,10-dione in solution was established by NMR spectroscopy and calculations using the Gaussian program.

Fluorination of benzene with the XeF 2 —BF 3 •Et 2 O system in acetonitrile at low temperatures affords fluorobenzene in 18% yield, the conversion of benzene being 92%. The rest products are di-, tri-, tetra-, and polyphenyls with different fluorination pattern. Toluene and chloro- and bromobenzenes are fluorinated predominantly at the ortho and para positions. Fluorination of 4-nitroanisole affords 2-fluoro-4-nitroanisole in 73% yield.

Formylation of pyrazole and 2,5-dimethylpyrazole gave a number of pyrazole-containing aldehydes, which can be used to obtain chromenes, tetrahydrochromenes, 1,4-dihydropyrano[2,3- c ]pyrazoles, pyrano[3,2- c ]chromenes, thiochromeno[4,3- b ]pyrans, pyrano[3,2- c ]-quinolines, and thiazolo[3,2- a ]pyridines.

Isothiazolothienopyridines have been prepared by a domino reaction (the SN2 reaction → the Thorpe-Ziegler reaction → the Thorpe-Guareschi reaction type) from disodium 4-cyanoisothiazole-3,5-dithiolate. By changing the order of addition of the alkylation reagents in the reaction with disodium 4-cyanoisothiazole-3,5-dithiolate both possible isomers of the isothiazolothienopyridines are synthesized. These isomers were further used in three-component domino reaction (the Knoevenagel reaction → the Michael reaction → the hetero-Thorpe-Ziegler reaction type) to obtain wide range of isomeric isothiazolothienopyranopyridines.

A simple and convenient preparative method for the synthesis of 3-cyano-4-difluoro- and -trifluoromethylpyridine-2(1 H )-thiones was developed. During studies of synthetic potential of these compounds, approaches to the synthesis of a number of annulated heterocyclic systems were suggested.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

This Letter describes a new microwave-assisted fluorination of azines using hydrated potassium fluoride in untreated DMSO under atmospheric conditions. It is thought that microwave irradiation promotes desolvation of the fluorine anion leading to halide nucleophilic substitution.

The reactions of ( S )- N -trifluoroacetyl-5-bromo-4-oxonorvaline methyl ester with vicinal mercaptonitriles afforded δ-hetaryl- N -trifluoroacetyl-substituted α-amino acids (hetaryl is thiazol-2-yl, 2-thienyl, or thieno[2,3- b ]pyridin-6-yl).

The reactions of N -(2-chloroacetyl)-α-amino acids with 3-cyanopyridine-2(1 H )-thiones afforded N -(3-aminothieno[2,3- b ]pyridin-2-ylcarbonyl)-α-amino acids. Heating of the latter smoothly produced 3,4-dihydropyrido[3",2":4,5]thieno[3,2- e ][1,4]diazepine-2(1 H ),5-diones in high yields.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Reactions of sodium derivatives of 2- and 3-thenoylacetaldehydes with cyanothioacetamide gave 2- and 3-cyano-6-thienylpyridine-2(1 H )-thiones, which were used in the synthesis of substituted 2-alkylthiopyridines, thieno[2,3- b ]pyridines, and other fused heterocycles.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

2-Benzoyloxy-2-phenylmalononitrile is formed instead of the expected oxime tosylate in the reaction of hydroxyiminoacetophenone withp-toluenesulfonyl chloride. The structure of the product was confirmed unambiguously by X-ray diffraction analysis.

Trimethylsilylation and methylation of 1 -hydroxybenzotriazole 3-oxide (1) proceed regioselectively and afford 1-trimethylsilyloxy- and 1-methoxybenzotriazole 3-oxides, respectively. The first compound easily undergoes fast hydrolysis and methanolysis, but does not react with nitroethane at 20 °C. A fast reversible 1,5-O,O-migration of the SiMe3 group is observed for this compound.