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.     

Aziridinylketones and their cyclic anils. 12

We have measured the PMR spectra of 5, 7-diaryl-1, 4-diazabicyclo[4. ].O]hept-4-enes. We have studied the structure of the 5-(4-nitrophenyl)-7-phenyl derivative by x-ray diffraction. We show that the six-membered heterocycle has the half-chair form. The 6-H and 7-H protons of the aziridine ring are trans, while the 7-aryl is exo relative to the six-membered ring. Introduction of substituents into the aromatic ring has practically no effect on the geometry of the bicycle.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1117–1124, August, 1994.For Communication 11, see [1].     

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.     

Effect of infection byVerticillium dahliae on the lipid complex of cotton seeds from varieties with contrasting resistance

The yields and fatty acid compositions of the free lipids and lipids weakly and strongly bound to proteins from seeds of cottonplant varieties resistant and susceptible to verticillium wilt have been determined and the changes in these indices in the seeds of the infected plants have been measured. It has been established that the seeds of healthy plants of the two varieties are similar in the qualitative compositions of the lipids and fatty acids but differ with respect the amounts of lipids in them bound with protein in different ways and with respect to the amounts of the individual fatty acids. The observed changes in the lipid and fatty-acid compositions depend on the degree of resistance of the variety to wilt.     

Electrohydraulic effect in heterodisperse water-plant systems. II. Chemical nature of the suspended particles

On the basis of the results of acid hydrolysis, chromatographic analysis of the hydrolysates, and a study of IR spectra, it has been established that the suspended particles liberated under the action of electrohydraulic shocks on heterodisperse water—plant systems consist of small fragments of the lignocarbohydrate complex of the plant tissue.