Superacid cyclization of esters of some bishomoisoprenoid acids

It is shown that on the superacid cyclization of esters of bishomobicyclogeranylgeranic and E,E-bishomofarnesic acids fully cyclized hydroxyesters are formed in good yield, while on the interaction of esters of 6-hydroxy- and 6-acyloxy-15-bishomobicyclogeranylgeranic acids with a superacid no carbocyclization takes place.     

Chemistry of polyenic and polyynic compounds

Conclusions A method is described for the synthesis of some cyano aldehydes, cyano esters, esters of dichloro acids, and esters of amino acids of the polyenic series.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 6, pp. 1334–1338, June, 1967.     

Synthesis of 3-Aryl-3-(Furan-2-yl)Propanoic Acid Derivatives,and Study of Their Antimicrobial Activity

Reactions of 3-(furan-2-yl)propenoic acids and their esters with arenes in Brønsted superacid TfOH affords products of hydroarylation of the carbon–carbon double bond, 3-aryl-3-(furan-2-yl)propenoic acid derivatives. According to NMR and DFT studies, the corresponding O,C-diprotonated forms of the starting furan acids and esters should be reactive electrophilic species in these transformations. Starting compounds and their hydroarylation products, at a concentration of 64 µg/mL, demonstrate good antimicrobial activity against yeast-like fungi Candida albicans. Apart from that, these compounds suppress Escherichia coli and Staphylococcus aureus.     

New path of dissociation of a tetrahedral intermediate during alkaline hydrolysis of benzimidates

A brief review is presented of the authors' studies carried out in recent years on the previously unknown rearrangement in the tetrahedral intermediate formed by alkaline hydrolysis of aryl esters of N-substituted benzimidic acids.Translated from Teoreticheskaya Éksperimental'naya Khimiya, Vol. 28, Nos. 5–6, pp. 400–406, September–December, 1992.     

Activation of a carboxy group by dialkyl pyrocarbonates. Synthesis of symmetrical anhydrides and aryl esters of N-protected amino acids using di-tert-butyl pyrocarbonate as condensing reagent

It has been shown that di-tert-butyl pyrocarbonate can be used as a condensing reagent in the production of anhydrides and some aryl esters of carboxylic acids. The synthesis of anhydrides and of phenyl, p-nitrophenyl, -naphthyl, and quinolin-8-yl esters of N-protected amino acids is described.Institute of Biological and Medicinal Chemistry, Academy of Medical Sciences of the USSR, Moscow. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 357–362, May–June, 1984.     

Gas-Chromatographic Determination of Organic Compounds in Water with the Use of Supercritical Fluid Extraction

Procedures were developed for the determination of some organic compounds (n-alkanes, polycyclic aromatic hydrocarbons, polychlorinated biphenyls, Cl,P,N-pesticides, phthalic acid esters, chlorophenols, aliphatic acids, and methyl esters of aliphatic acids) in water on the basis of direct supercritical fluid extraction with the subsequent gas-chromatographic analysis of the entire extract without using organic solvents. The detection limits were 10^–11–10^–7% depending on the nature of the analyte.     

Triterpenoids from Abies species. IV. New triterpene acids from the needles of Abies sibirica

Four new triterpene acids of the mariesiic acid series have been isolated from an extract of the needles of the Siberian fir in the form of their methyl esters, and their structures have been established on the basis of chemical transformations, spectral characteristics, and x-ray structural analysis.Novosibirsk Institute of Organic Chemistry, Siberian Branch, USSR Academy of Sciences. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 824–831, November–December, 1987.     

Synthesis of homologs of 2-aminoethylphosphonic acid

Conclusions Some homologs of 2-aminoethylphosphonic acid were synthesized by the addition of dialkyl phosphites to nitroolefins and the subsequent reduction of the thus obtained esters of 2-nitroethylphosphonic acid to the amino esters. Hydrolysis of the latter gave the free acids.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 6, pp. 1382–1385, June, 1973.     

Choline esters of alkylenebisphosphonic acids

The reaction of the acid chlorides of alkylenebisphosphonic acids with ethylene glycol and ethylene chlorohydrin gave ethylene glycol and -chloroethyl esters of alkylenebisphosphonic acids. The quaternization of these products leads to choline esters of alkylenebisphosphonic acids.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 6, pp. 1424–1429, June, 1990.     

An unexpected reaction of 2-vinyloxyethyl isothiocyanate with halocarboxylic acids

Reactions of 2-vinyloxyethyl isothiocyanate with aliphatic halocarboxylic acids give rise to their 1-(2-isothiocyanatoethoxy)ethyl esters in quantitative yields. An unusual rearrangement of 1-(2-isothiocyanatoethoxy)ethyl chloro(bromo)acetate and 3-bromopropanoate to 5-aza-7-chloro(bromo)-4-oxo-3-thiaheptanoic and to 6-aza-8-bromo-5-oxo-4-thiaoctanoic acids, respectively, was observed. Monohalocarboxylic acids and their esters were shown to readily alkylate l,3-oxazolidine-2-thione to form the same thiaheptanoic and thiaoctanoic acids and their esters.Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 350–354, February, 1993.     

Electrochemical oxidation of some thiobenzyl esters of P(III) acids

Electrochemical oxidation of a series of thiobenzyl esters of P(III) acids is studied and its catalytic character is shown. The process occurs irreversibly and the compounds formed are identical with the products of the reaction of thiobenzyl esters of P(III) acids with molecular oxygen.Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 6, pp. 1114–1115, June, 1993.     

Studies on pyran,its analogs,and related compounds

The action of guanidine on esters of chromone-2-carboxylic acids leads to the opening of the pyrone ring and to the formation of hydantoin derivatives — 2-imino-5-(2-hydroxybenzoylmethylene)tetrahydroimidazol-4-ones — in addition to other reaction products.Translated from Khimiya Geterotsiklicheskikh Soedinenii, Vol. 6, No. 7, pp. 874–875, July, 1970.     

Morpholinization of aminoacyloxy acids and hydroxyacylamino acids and their esters under mass spectrometry conditions

Summary 1. Free hydroxyacylamino acids and their methyl esters, and also free aminoacyloxy acids, morpholinize under mass spectrometry conditions.2. In the mass spectrometry of methyl esters of aminoacyloxy acids and tert-butyl esters of aminoacyloxy acids and hydroxyacylamino acids no morpholinization takes place. These compounds behave similarly to the esters of acylated peptides and depsipetides.Khimiya Prirodnykh Soedinenii, Vol. 3, No. 5, pp. 325–327, 1967     

Influence of infection by Verticillium dahliae on the cuticular lipids of the leaves of cotton plants of variety 175

The composition of the cuticular lipids of young leaves of cotton plants of the wilt-resistant variety 175-F has been determined and it has been established that on artificial infection of the plant with cotton wilt(Verticilliuim dahliae) the component composition of these lipids did not change but the level of the 18:0, 18:1, and 18:2 acids in esters of fatty acids with alkanol, sterols, and triterpenols fell.Institute of the Chemistry of Plant Substances, Uzbek. Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 765–768, November–December, 1991.     

Reaction of furan and its derivatives with ethyl diazoacetate in the presence of copper sulfate

Conclusions The thermocatalytic reaction of ethyl diazoacetate with alkylfurans and the esters of furylcarboxylic acids leads to the formation of the ethyl esters of the corresponding trans, trans 1, 3-alkadien-5-onecarboxylic acids, while reaction with furan leads to the formation of a mixture of a similar ester and 6-ethoxycarbonyl-2-oxabicyclo [3.1. 0]-3-hexene, which is easily isomerized to the former.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 10, pp. 2342–2345, October, 1972.     

Reaction of esters of thio acids of trivalent arsenic with organomagnesium compounds

Conclusions Depending on the molar ratios, the esters of the thio acids of trivalent aresnic are alkylated by organomagnesium compounds to give the corresponding tertiary arsines or the esters of the thio acids of trivalent arsenic.Deceased.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 4, pp. 963–965, April, 1972.     

Acids and their functionally substituted esters fromAmaranthus cruentus seed oil

The acid composition of seed oil ofAmaranthus cruentus and the synthesis of their glycidyl and pyridinecontaining esters are studied. It is demonstrated that 67% of the total acids are C₁₈-polyunsaturated linoleic and linolenic. A new method for preparing glycidyl esters of C₁₈-unsaturated carboxylic acids is developed by reacting their salts with ECG in an aprotic medium to produce the corresponding glycidyl esters. The reaction of the glycidyl esters and pyridine salts with carboxylic and phosphonic acids produces the propanolpyridine esters of the acids that combine the properties of the acids and pyridinium salts and are promising in the search for biologically active compounds.A. E. Arbuzov Institute of Organic and Physical Chemistry, Kazan' Scientific Center, Russian Academy of Sciences. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 217–219, May–June, 2000.     

The composition of the organic acids of CO2 extracts of some spice-aromatic plants

Summary 1. It is desirable to analyze the composition of the organic acids of CO₂ spice extracts after their preliminary separation into individual groups according to their physicochemical properties: steam-volatile, ester-bound obtained after the hydrolysis of esters of nonglyceride nature, and acids forming components of the triglycerides.2. Characteristic for the fraction of steam-volatile free acids and for the ester-bound acids in the CO₂ extracts obtained after the hydrolysis of esters of nonglyceride nature are the C₁–C₇ low-molecular-weight saturated acids of the alipatic series: formic, isovaleric, valeric, caproic, etc. The higher fatty acids present include acids with even and odd numbers of carbon atoms from C₈ to C₁₈ and also acids with saturated and unsaturated bonds.3. The compositions of the lower acids in the extracts of all the samples studied are qualitatively very similar. Their quantitative compositions differ fundamentally. At the same time, differences both in the qualitative and in the quantitative compositions of the glyceride acids of the samples investigated are more pronounced. This is due to the circumstance that fruit was subjected to extraction in one case and leaves and rhizomes in another.Krasnodar Scientific-Research Institute of the Food Industry. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 763–767, November–December, 1977.     

Synthesis of methyl esters of 5-amino-4-(substituted amino)-2-methylthio-7H-pyrrolo[2,3d]-pyrimidine-6-carboxylic acids

The optimum route for the synthesis of methyl esters of N-[(4-substituted amino)-5-cyano-2-methylthiopyrimidin-6-yl]amino acids (which are starting materials for preparing the methyl esters of the corresponding 5-amino-4-(substituted amino)pyrrolo[2,3-d]pyrimidine-6-carboxylic acids) is via subsequent reactions of 4,6-dichloro-2-methylthiopyrimidine-5-carbonitrile with amines and methyl glycinate. In some examples, the reaction of methyl N-(4-chloro-2-methylthio-6-pyrimidinyl)aminoacetate with amines occurs to give the corresponding acid amides. The previously unknown synthesized derivatives of pyrimidin-6-yl amino acids and 4,5-diaminopyrrolo[2,3-d]pyrimidine- 6-carboxylic acids possess fungicidal properties.Vilnius University, Vilnius 2006, Lithuania. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No 7, pp. 955–961, July, 2000.     

Thermal decomposition of 2-hydroxyalkylthiol esters of phosphorus acids

Conclusions The decomposition of the 2-hydroxyalkylthiol esters of phosphorus acids at atmospheric pressure leads to alkylene sulfides and the corresponding phosphorus acids. The direction of the reaction for the thermal decomposition of these esters in vacuo depends on the structure of the substituents on the phosphorus atom.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 11, pp. 2625–2627, November, 1976.