A Facile Synthesis of Novel Cyclic Esters of γ‐Keto Acid Derivatives by Heck Coupling Reaction

γ‐Keto acids and esters are highly useful compounds in organic synthesis, because a number of five‐membered carbocycles and various other heterocycles can be readily obtained from them. A number of γ‐keto acids derivatives have been synthesized with high yield by Heck coupling reaction with different alkenes using Pd(OAc)₂ as catalyst in dioxane solvent. The obtained products were characterized by elemental analysis, IR, proton NMR, and mass spectral studies.     

Synthesis of substituted 2-amino-3-cyanopyrroles

A method was worked out for the preparation of substituted 2-amino-3-cyanopyrroles from N-acyl-α -amino ketones and malononitrile. Acyl derivatives of 2-amino-3-cyanopyrroles were obtained. A number of Mannich bases were synthesized by aminomethylation of 2-acetamido-3-cyano-4-phenylpyrrole.     

2-Bromomethyl derivatives of benzofuran and indole and their reactions with some nucleophilic reagents

The corresponding 2-bromomethyl derivatives of benzofuran and indole were obtained by bromination of 2-methyl-3-carbethoxy-5-methoxybenzofuran and 1,2-dimethyl-3-earbethoxy-5-methoxyindole with N-bromosuccinimide. A number of alkyl(aryl)thiomethyl and dialkylaminomethyl derivatives were obtained by reaction of the 2-bromomethyl derivatives with nucleophilic reagents.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 308–311, March, 1973.     

Synthesis of actinomycin D analogs: XXIII. Actinocin derivatives containing azacrown fragments

A number of actinocin amides containing residues of aza-15-crown-5 and aza-18-crown-6 where crown fragments were separated from the heterocyclic chromophore by the residues of ω-amino acids were obtained as actinomycin D models.     

Blood flow and oxygen transfer rate of an outside blood flow membrane oxygenator

We evaluated effects of the number of tied hollow fibers of an outside blood flow membrane oxygenator with cross-wound hollow fibers on the blood flow pattern and oxygen transfer rate. The number of tied hollow fibers in a bundle was varied from one to six, and the blood flow pattern was observed by X-ray computed tomography. The oxygen transfer rate and blood pressure drop were measured by in vitro experiments using bovine blood. Uniform blood flow patterns were obtained for each number of tied hollow fibers. A decrease in the number of tied hollow fibers caused more effective contact of blood with the tied hollow fibers and oxygen transfer rate was enhanced, demonstrating that single hollow fiber was the most effective. Empirical equations were obtained based on these results and optimum structure parameters of the membrane oxygenator were determined by simulation analysis. Optimum membrane surface area and axial jacket length of the oxygenator were 3.0 m² and 320 mm, respectively, at a hollow fiber outside diameter of 250 μm.     

Synthesis and spectral-luminescence properties of 7-diethylamino-4-(2-arylethenyl)coumarins

A number of 7-diethylamino-4-(2-arylethenyl)coumarins were obtained by condensation of 7-diethylamino-4-methylcoumarin with aromatic aldehydes, while only a product of addition to the carbon—nitrogen double bond is formed with benzalaniline. The spectral-luminescence properties of the compounds obtained were investigated.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 319–322, March, 1991.     

Synthesis and Transformations of Norbornyl Acrylates

A simple and more environmentally friendly procedure than that traditionally used was developed for preparation of esters consisting in acrylic acid addition to bicyclo[2.2.1]hept-2-ene and its 5-alkyl derivatives. The acrylates obtained were subjected to hydrogenetion followed by hydrolysis of propionic acid esters. A number of new compounds was obtained; some among them possess a pleasant odor.     

Alkylation of 3-cyano-2-oxopyridine derivatives

A number of N- and O-alkylpyridines were obtained by alkylation of 3-cyano-2-oxopyridines with alkyl halides and diazomethane.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1089–1092, August, 1976.     

The condensation productions of chloral and the amides of organophosphoric acids

Summary A number of monosubstituted amides (RO)₂P(O)NHCH(OH)CCl₃ were obtained by the reaction of chloral with dialkylphosphoric acids, and subsequently characterized.     

Anthra[1,2-b]furan and 1h-naphth[2, 3-g]indole derivatives

A number of previously inaccessible anthra[1,2-b]furan and 1H-naphth[2,3-g]indole derivatives were obtained by condensation of 1,4-anthraquinone with acetoacetic ester and its analogs. Quinones of the anthra[1,2-b]furan series were obtained by oxidation of the methoxy derivatives of anthra[1,2-b]furan.Translated from Khimiya Geterotsiklicheskikh Soedtaenii, No. 8, pp. 1027–1029, August, 1972.     

Anhydrides and phenylimides of 4-(5-aryl-2-oxazolyl)naphthalic acids

A number of 4-(5-aryl-2-oxazolyl)naphthalic anhydrides were obtained by condensation of 4-chloroformylnaphthalic anhydride with -aminomethyl aryl ketones and subsequent cyclization of the resulting amides; N-phenylimides were obtained from the anhydrides by reaction with aniline. The relationship between the structures of the substances obtained and their UV and luminescence spectra was investigated.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1331–1333, October, 1973.     

Heterocyclic nitro compounds

A number of triazolylpropanones were synthesized by oxidation of 1-(2-hydroxypropyl)-3-nitro-5-R-1,2,4-triazoles obtained by condensation of 3-nitro-5-R-1,2,4-triazoles with propylene oxide. Similar triazolylbutanones were obtained by reaction of 3-nitro-5-R-1,2,4-triazoles with methyl vinyl ketone.See [1] for communication XIX.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 991–994, July, 1976.     

Research on furan acetal compounds. VIII. Synthesis of (2-furyl)diacetamidomethanes

A number of diacetamidomethanes were obtained by condensation of 5-substituted furfurals with acetamides. Previously undescribed 1,3-dioxepanes were synthesized by reaction of the indicated aldehydes with 1,4-butanediol.See [1] for communication VII.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 162–163, February, 1976.     

Isocyanates of the quinoline series

The isocyanates obtained by rearrangement of azides of quinaldic and quinoline-2,4-di-carboxylic acids exist as trimers. A number of urethanes were obtained by the decomposition of these azides ta the presence of alcohols. The possibility of the use of the azide of quinoline-2,4-carboxylic acid to obtain polymers was investigated.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 527–528, April, 1972.     

Synthesis of C-glycosylindazoles by 1,3-dipolar cycloaddition of α-Diazoketoses to benzynes

A number of C-glycosylindazoles were prepared by 1,3-dipolar cycloaddilion of several α-diazoketoses to benzyne. When the cycloaddition reaction was carried out with benzyne derivatives the two possible isomeric indazoles were obtained in most of the cases. Structural assignments were made on the basis of nmr data.     

Asymmetric Syntheses Aided by Biocatalysts

This article summarizes the achievements of the authors‘ group in the area of biocatalyst-catalyzed organic reactions in recent 10 years. A strain of Geotrichum sp. obtained by screeninu is capable of stereoselectlvely reducing a number of carbonyl compounds. In many cases, the stermghemistry is complementary with that obtained by baker‘ s yeast. Therefore, this microorganism provides a useful pathway to the preparation of alcohol eompounds with specific configurations. On the other hand, a nmmber of plant sourees have been screened for oxynitrilases and the hydrocyanation reactions of various arylcarboxalde-hydes have been investigated.A“micro-aqueous reaction system“ was invented,by which a serles of novel optically active cyanohydrins were prepared.On this hasis,a high through-put comtimasous reaction system has been designed.This paper also deseribes examples of the syntheses of bio-active compounds by using the optieally active compounds obtained from the above mentioned catalytic reactions as precursors.     

Synthesis of 5-(1,2,5-oxadiazol-3-yl)-1H-etrazoles from 3-cyano-1,2,5-oxadiazoles

A number of 5-(1,2,5-oxadiazol-3-yl)-1H-tetrazoles were obtained in high yields by reactions of 3-cyano-1,2,5-oxadiazoles with sodium azide or by nitrosation of furazan-based amidrazones, which are easily prepared from the same starting reagents.     

Stereochemistry of bisdioxolane systems

A number of diastereomers of cyclic diacetals of succinaldehyde were obtained by transacetalation of succinaldehyde bis(dimethylacetal) with the optical antipodes of tosylglycerol. The configurations of the products were determined.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1608–1610, December, 1973.     

Synthesis of 3-methyl-4-(5-R-1H-1,2,4-triazol-3-yl)-1,2,5-oxadiazoles

A number of 3-methyl-4-(5-R-1H-1,2,4-triazol-3-yl)-1,2,5-oxadiazoles were obtained in high yields by thermal dehydration of acylated 4-methyl-1,2,5-oxadiazole-3-carboxamide hydrazones.     

Investigation of free radicals from N-substituted dihydrophenazines

A number of N-substituted dihydrophenazines were synthesized. New, neutral radicals of the phenazine series were obtained by oxidizing them with lead dioxide, and several of their properties were studied (EPR spectra and electronic spectra).Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1428–1431, October, 1970.