Synthesis of 2-Chloromethyl-5-aryl-, 2-Chloromethyl-5-(5-methyl-2-furyl)-, and 2-Chloromethyl-5-(1,5-dimethyl-2-pyrrolyl)-1,3,4-oxadiazoles from Tetrazole Derivatives

Acetylation of 5-aryltetrazoles, 5-(5-methyl-2-furyl)tetrazole, and 5-(1,5-dimethyl-2-pyrrolyl)tetrazole with chloroacetyl chloride was studied.__________Translated from Zhurnal Prikladnoi Khimii, Vol. 78, No. 5, 2005, pp. 787–789.Original Russian Text Copyright © 2005 by Baranov, Tsypin, Malin, Laskin.     

Spiroheterocyclic Compounds Based on 2-Bromobutanolides

Bromination of ethyl 5-alkoxymethyl-2-oxotetrahydrofuran-3-carboxylates afforded ethyl 5-alkoxymethyl-3-bromo-2-oxotetrahydrofuran-3-carboxylates which reacted with thiourea, substituted thioureas, benzimidazole-2-thiol, and benzothiazole-2-thiol to give new heterocyclic compounds.__________Translated from Zhurnal Organicheskoi Khimii, Vol. 41, No. 4, 2005, pp. 590–593.Original Russian Text Copyright © 2005 by Kochikyan.     

Desulfurization of 2-Thioxo-1,2,3,4-tetrahydropyrimidin-4-ones with Oxiranes and 2-Haloacetonitriles

A procedure was developed for the synthesis of tetrahydropyrimidine-2,4-diones by desulfurization of 2-thioxo-1,2,3,4-tetrahydropyrimidin-4-ones with oxiranes or 2-haloacetonitriles in polar solvents in the presence of a base.__________Translated from Zhurnal Organicheskoi Khimii, Vol. 41, No. 4, 2005, pp. 617–619.Original Russian Text Copyright © 2005 by Novakov, Orlinson, Navrotskii.     

Synthesis of 6-Methyl-4-(1-methyl-2-buten-1-yl)-2-(2-cyclohexen-1-yl)- and 6-Methyl-4-(1-methyl-2-buten-1-yl)-2-(1-cyclohexen-1-yl)anilines

Alkenylation of 6-methyl-2-(2-cyclohexen-1-yl)- and 2-(1-cyclohexen-1-yl)anilines with piperylene in the presence of AlCl₃ and transformation of the resulting cyclohexenylanilines into carbazole structures were studied.__________Translated from Zhurnal Prikladnoi Khimii, Vol. 78, No. 3, 2005, pp. 441–443.Original Russian Text Copyright © 2005 by Gataullin, Ishberdina, Sotnikov, Abdrakhmanov.     

2-Hydroxymethyl-2-propyl-1,3-propanediol in the Synthesis of Phospholipids

New representatives of nonglycerol polyol phospholipids were synthesized from 2-hydroxymethyl-2-propyl-1,3-propanediol through intermediate phosphoramidites and cyclic phosphites obtained from isopropylidene derivative of the title triol. Treatment of these intermediate products with sulfur or selenium afforded the corresponding thio- and selenophosphates which were converted into lipids by direct acylation with higher carboxylic acid chlorides.__________Translated from Zhurnal Organicheskoi Khimii, Vol. 41, No. 7, 2005, pp. 983–987.Original Russian Text Copyright © 2005 by Savin, Kamneva.     

Reaction of 2-Alkoxypropenals with 2-Aminoethanethiol and Ring-Chain Tautomerism of the Resulting 2-(1-Alkoxyvinyl)-1,3-thiazolidines

2-Alkoxypropenals react with 2-aminoethanethiol to give tautomeric mixtures of the corresponding 2-(1-alkoxyvinyl)-1,3-thiazolidines and 2-(2-alkoxy-2-propenylideneamino)ethanethiols in quantitative yield. The state of the ring-chain tautomeric equilibrium depends on the polarity and acidity of the medium and initial reactant ratio, and it does not change on raising the temperature and is only slightly affected by microwave irradiation.__________Translated from Zhurnal Organicheskoi Khimii, Vol. 41, No. 4, 2005, pp. 529–534.Original Russian Text Copyright © 2005 by Keiko, Funtikova, Stepanova, Larina.     

4,4-Dialkoxybutan-2-ones as Synthons

The review considers the synthetic potential of 4,4-alkoxybutan-2-ones which are promising synthons available from diacetylene-containing industrial gases. The reactivity of 4,4-dialkoxybutan-2-ones toward mono- and difunctional reagents, as well as in cycloaddition processes, is discussed.__________Translated from Zhurnal Organicheskoi Khimii, Vol. 41, No. 1, 2005, pp. 9–32.Original Russian Text Copyright © 2005 by Maretina.     

Synthesis and Properties of Substituted 2-Amino-5-nitrosobenzylamines

Substituted nitrosobenzylamines were synthesized by cyclocondensation of hydroxyimino-β-diketones with 4-dialkylamino-2-butanones.__________Translated from Zhurnal Organicheskoi Khimii, Vol. 41, No. 1, 2005, pp. 57–59.Original Russian Text Copyright © 2005 by Semichenko, Gavrilova, Suboch.     

Nitration of Some 3-(2-Furyl)-2-propenones with Dinitrogen Tetraoxide

Nitration of 3-(2-furyl)-2-propenones with dinitrogen tetraoxide leads to the corresponding 3-(4-nitro-2-furyl)-2-propenones. If the furyl group contains a substituent in position 5, the nitration occurs at the side chain to afford 3-(5-R-2-furyl)-2-nitro-2-propenones.__________Translated from Zhurnal Organicheskoi Khimii, Vol. 41, No. 3, 2005, pp. 431–436.Original Russian Text Copyright © 2005 by Sitkin, Klimenko.     

Synthesis of 5-Amino-4-(4-aryl-2-thiazolyl)-2,3-Dihydro-2-Pyrrolones

A method was developed for preparation of 5-amino-4-(4-aryl-2-thiazolyl)-2,3-dihydro-2-pyrrolones by alkylation of 4-aryl-2-thiazolylacetonitriles by N-substituted chloroacetamides in the presence of K₂CO₃. In 1-(1-naphthyl)-substituted pyrrolones atropoisomerism was observed.__________Translated from Zhurnal Organicheskoi Khimii, Vol. 41, No. 2, 2005, pp. 266–269.Original Russian Text Copyright © 2005 by Resnyanskaya, Tverdokhlebov, Tolmachev, Volovenko.     

Synthesis of 5-Hydroxy-1,3-benzoxathiol-2-one and 2-Amino-1,3-benzothiazol-6-ol Derivatives from Chrysenequinonecarboxylic Acid

Diterpenoid 5-hydroxy-1,3-benzoxathiol-2-one and 2-amino-1,3-benzothiazol-6-ol derivatives were synthesized by reaction of methyl chrysenequinonecarboxylate with thiourea.__________Translated from Zhurnal Organicheskoi Khimii, Vol. 41, No. 6, 2005, pp. 849–852.Original Russian Text Copyright © 2005 by Tret’yakova, Flekhter, Galin, Shul’ts, Tolstikov.     

Reaction of (2-Nitro- and 2-Bromo-2-nitroethenyl)phosphonates with 1,3-Cyclohexadiene

Specific features of the reactions of bis(chloroethyl) 2-nitro- and 2-bromo-2-nitroethenylphosphonates with 1,3-cyclohexadiene were studied. It was found that the reaction with 2-nitroethenylphosphonate occurs stereoselectively and provides bis(2-chloroethyl) endo-(3-nitrobicyclo[2.2.2]oct-5-en-2-yl)phosphonate. 2-Bromo-2-nitroethenylphosphonate under the same conditions gives a mixture of the endo and exo isomers of the corresponding nitrobicyclooctenes. Enhanced tendency of adducts derived from gem-bromonitroethenyl-phosphonates for intramolecular transformations, such as dehydrohalogenation and aromatization, under the cycloaddition conditions was revealed.__________Translated from Zhurnal Obshchei Khimii, Vol. 75, No. 7, 2005, pp. 1106–1110.Original Russian Text Copyright © 2005 by Anisimova, Kuzhaeva, Berkova, Deiko, Berestovitskaya.     

Reactions of 2-Butylsulfanyl-2-alkenals with Alcohols and Water

2-Butylsulfanyl-2-alkenals react with alcohols at room temperature in the presence of acid catalysts to give 45–90% of the corresponding acetals. Acetals derived from 2-butylsulfanylpropenal readily undergo hydrolysis at the vinylsulfanyl group (20°C, catalysis by HCl or TsOH) with formation of 2-oxopropionaldehyde O,O- or O,S-acetals in 70–90% yield. Unlike 2-butylsulfanyl-2-propenal O,O-dialkyl acetals, the initial aldehydes and 2,4-dinitrophenylhydrazones derived therefrom are stable to hydrolysis under analogous conditions: the vinyl sulfide moiety remains unchanged even under considerably more severe conditions (100°C, 3 h; HCl, H₂SO₄, CF₃SO₂OH, or TiCl₄).__________Translated from Zhurnal Organicheskoi Khimii, Vol. 41, No. 6, 2005, pp. 832–836.Original Russian Text Copyright © 2005 by Keiko, Chuvashev, Stepanova, Larina.     

Condensation of Benzoxa(thia)zolyl-2-guanidines with Dicarbonyl Compounds

Heterocyclizations of benzoxa(thia)zolyl-2-guanidines with β-dicarbonyl compounds, such as diketones and derivatives of acetoacetic ether, were studied.__________Translated from Zhurnal Obshchei Khimii, Vol. 75, No. 2, 2005, pp. 322–325.Original Russian Text Copyright © 2005 by Shikhaliev, Kryl’skii, Kovygin, Verezhnikov.     

3-Alkyl-2-[3(4)-pyridyl]-5-(2-vinyloxyethoxymethyl)-oxazolidines

1-Alkylamino-3-(2-vinyloxyethoxy)-2-propanols react with 3-and 4-pyridinecarbaldehydes to give equimolar mixtures of cis- and trans-3-alkyl-5-(2-vinyloxyethoxymethyl)-2-[3(4)-pyridyl]oxazolidines.__________Translated from Zhurnal Organicheskoi Khimii, Vol. 41, No. 1, 2005, pp. 104–108.Original Russian Text Copyright © 2005 by Kukharev, Stankevich, Lobanova, Klimenko, Kukhareva.     

Interaction of 2-Aminoindoles with Tetracyanoethylene. 2. 3-Dicyano-methylene-2-iminoindolines

3-Dicyanomethylene-2-iminoindolines are obtained on interacting 2-aminoindoles with tetracyanoethylene in acidic medium. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1515–1520, October, 2005.     

Regular Trends in Nucleophilic Substitutions in 2-Alkylamino-4-chloronitrobenzenes

The effect of substituents in position 2 on the reactivity of 2-alkylamino-4-chloronitrobenzenes in nucleophilic substitution by N-nucleophiles of various character was studied.__________Translated from Zhurnal Organicheskoi Khimii, Vol. 41, No. 2, 2005, pp. 224–227.Original Russian Text Copyright © 2005 by Zotova, Kushakova, Kuznetsov, Rodin, Garabadzhiu.     

Synthesis of Substituted 2-Methyl-4-quinolyl Isothiocyanates and 4-Mercaptoquinolines

Synthesis was performed of substituted 2-methyl-4-quinoline thiouronium salts by reaction of 2-methyl-4-chloroquinolines with thiourea. The alkaline hydrolysis of these salts afforded the corresponding 2-methyl-4-quinolyl- isothiocyanates and 2-methyl-4-mercaptoquinolines.__________Translated from Zhurnal Organicheskoi Khimii, Vol. 41, No. 5, 2005, pp. 783–785.Original Russian Text Copyright © 2005 by Avetisyan, Aleksanyan, Ambartsumyan.     

Synthesis of Dimethyl 2-(2-Alkyl-1,3-diaryl-3-oxopropyl)malonates and Their Reactions with Amines

Zinc enolates generated from 1-aryl-2-bromoalkanones and zinc react with dimethyl 2-(1-arylmethylene)malonate to form dimethyl 2-(2-alkyl-1,3-diaryl-3-oxopropyl)malonates. The latter react with benzylamine or cyclohexylamine to form the corresponding disubstituted amides, while the reactions with piperidine, morpholine, and p-methoxyaniline provide monosubstituted amides of the corresponding target derivatives.__________Translated from Zhurnal Obshchei Khimii, Vol. 75, No. 4, 2005, pp. 636–641.Original Russian Text Copyright © 2005 by Shchepin, Korzun, Poroshina.     

On the Mechanism of Intramolecular Cyclization of Dialkyl(2-propynyl)[3-alkenyl(or aryl)-2-propynyl]-ammonium Salts

Given are experimental data indicating that base-catalyzed intramolecular cyclization of ammonium salts containing a 2-propynyl-like group together with a 3-alkenyl- or 3-aryl-2-propynyl group follows a concerted mechanism involving the 3-alkenyl- or 3-aryl-2-propynyl moiety as π⁴-fragment.__________Translated from Zhurnal Organicheskoi Khimii, Vol. 41, No. 3, 2005, pp. 369–371.Original Russian Text Copyright © 2005 by E. Chukhadzhyan, Gevorkyan, El. Chukhadzhyan, Kinoyan.