Use of ultrasound in heterocyclic chemistry (review)

We review literature data on synthesis and conversions of heterocyclic compounds using ultrasonic treatment.We analyze the effect of ultrasound on organic reactions involving participation of heterocyclic compounds.A. N. Kosygin State Technical Academy, Moscow 117918. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 723–755, June 1994. Original article submitted December 22, 1993.     

Synthesis and ring-chain isomerism of acid chlorides and amides of 2-(2-pyridyl and 2-quinolylcarbonyl) benzoic acids

The reaction of 2-(2 pyridytcarbonyl)benzoic acid with thionyl chloride affords an unexpected product of the intramolecular acylation of the pyridine nitrogen atom, namely, 6,11-dioxo-6,11-dihydrobenzo[blquinotizinium chloride. At the same time, 2-(2-quinotylcarbonyl)benzoic acid forms the expected cyclic acid chloride, namely, 3-(2-gitinotyl)-3-chlorophthalide in this reaction. Both compounds acylate ammonia and primary amines, including those with bulky alkyl groups (tert-butyl, 1-adamantyl, and 1,1,3,3-tetramethylbutyl) with the formation of 2-R-3-hydroxy-3-(2pyridyl- or 2-quinolyl)isoindolines. The protonation of the pyridine nitrogen atom of N-(1,1,3,3-tetramethylbutyl)-2-(2pyridylcarbonyl)benzamide, obtained in the open amide form, is accompanied by the closing of the isoindotinone ring; the deprotonation is accompanied by ring opening.Riga Technical University, Riga LV-1048. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 499–504, April, 1994. Original article submitted March 17, 1994.     

5-[5-R-furfurylidene]-2,2-dimethyl-1,3-dioxane-4,6-diones 5. Nucleophilic replacement of halogen in the furan ring

Halogen in positions 3 and 5 of the furan ring in ftirfurylidenedioxanediones is readily replaced by dithiocarbonate, dithiocarbatnate, dithiophosphate, thiocyanate, and azide anions, and by thiourea, and secondary and tertiary amines. The conformation of the initial halogen derivative is retained in the substitution products.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 327–334, March, 1994.     

Hydroxyl-containing mesogens. Synthesis and liquid-crystalline properties of 2-o-hydroxyarylpyrimidines

We have synthesized 5-alkyl(alkoxy)-2-(o-lzydroxy-p-alkoxyphenyl)pyrimidines and considered the effect of the OH group on the inesomorphism. We have found that in binuclear o-hydroxyarylpyrimidines, an ortho OH group forming an intramolecular hydrogen bond increases T_mp, inhibits the appearance of nematic properties, and promotes the appearance of a smectic A.Translated from Khimiya Geterotsiklicheskikh Soedinenii, Vol. 30, No. 1, pp. 90–92, January, 1994.     

Electrohydraulic effect in aqueous-plant heterodisperse systems III. A study of the composition of the solid phase and the aqueous phase

By changing the conditions of the electrohydraulic treatment of aqueous plant heterodisperse systems comparatively high degradation of the lignin component of plant tissue has been achieved. In addition to free monosaccharides, their reduced forms have been detected in the aqueous phase. Institute of the Chemistry of Plant Substances, Academy of Sciences of the Republic of Uzbekistan, Tashkent, fax (3712) 89 14 75. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 795–798, November–December, 1994.     

Electron-impact mass spectra of natural phenylethanoids

The electron-impact mass spectra of a number of phenylpropanoids and iridoid glycosides containing a phenylethanoid fragment in their structure have been studied. This has revealed features of the formation of fragments of 4-hydroxyphenylethyl and 3,4-dihydroxyphenylethyl alcohols and also of fragments of phenylethylamine and indolylethylamine derivatives present in the structures of the compounds investigated.     

Some kinetic features of the hydrolysis of protopectin

Some features of the kinetics of the hydrolysis of apple protopectin have been studied on the basis of an analysis of monosaccharide residues of the pectin substances and determinations of characteristic viscosity. It has been shown that the fine regulation of the physicochemical parameters of the hydrolysis of protopectin leads to the formation of pectin substances with different properties.     

Lipids of cottonseed and palm oils and compositions based on them

The phsicochemical indices and the fatty-acid and triacylglycerol compositions of cottonseed and palm oils, of cottonseed oil hydrogenate, and of compositions based on them have been determined with the aid of IR and UV spectroscopies, GLC analysis, and chemical transformations. The compositions and amounts of the main classes of lipids in the initial oils and the hydrogenate have been studied. It has been found that in the process of hydrogenation the amount of oxygenated components falls. The work was conducted with the financial support of the Uzbek Fund for Fundamental Investigations.