Synthesis of 2-amino-3-carbethoxy-1-hydroxyindoles

A general method is described for the synthesis of 2-amino-3-carbethoxy-l-hydroxyindoles by the reductive cyclization of 2-nitrophenylcyanoacetates using zinc and acetic acid at temperatures of 15–28°.     

Synthesis and properties of azoles and their derivatives

The 1,3-dipolar cycloaddition reaction of nitrile N-oxides, and also the thermal condensation of arylhydroxamic acid chlorides with unsaturated derivatives of the adamantane series leads to the corresponding 3,5-disubstituted isoxazolines and isoxazoles.     

Synthesis and properties of azoles and their derivatives

Thermal condensation of 1-cyanoadamantane with arylhydroxamic acid chlorides gave 5-(1′-adamantyl)-1,2,4-oxadiazoles containing aromatic groupings in the 3 position. The same 1,2,4-oxadiazoles were synthesized by reaction of the N-oxides of the appropriate nitriles with adamantane-1-carboxylic acid methyl imino ester obtained from 1-cyanoadamantane. The corresponding 5-(1′-adamantyl)-3-substituted 1,2,4-oxadiazoles were obtained by condensation of the latter with amidoxines.     

Synthesis and properties of azoles and their derivatives

A method is proposed for the synthesis of 1-(2-cyanoethyl)-2-substituted 2-imidazolines; the method is based on reaction of N-(2-cyanoethyl)ethylenediamine with the hydrochlorides of methyl imino esters of carboxylic acids.See [1] for communication XVI.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1674–1675, December, 1973.     

Synthesis and properties of azoles and their derivatives

The corresponding mono- and bisheterocyclic derivatives of adamantane were obtained by reaction of the dinitrile or diimino ester of adamantane-1,3-dicarboxylic acid with ethylenediamine and related compounds.See [1] for communication XXIX.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1654–1657, December, 1976.     

Synthesis of substituted 4H-imidaz o[1, 5 -a] benzimid azoles

1-Phenyl-4-benzylimidazo[1,5-a]benzimidazole (III) was synthesized and subjected to acetylation, azo coupling, and the Vilsmeier reaction at the 3 position. 1-Phenyl-3-cyano-4-benzylimidazo[l,5-a]benzimidazole (X) was also obtained.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 395–397, March, 1973.See [1] for communication VII. This system was designated 4H-imidazo[5,1-b]benzimidazole in the preceding communications of this series.The UV spectra of alcohol solutions of the compounds were recorded with SF-4 and EPS-3 spectrophotometers. The PMR spectra of CDCl₃ solutions were recorded with a JNM-4H-100 spectrometer with an operating frequency of 100 MHz with tetramethylsilane as the internal standard. The IR spectra were recorded with a UR-10 recording spectrophotometer.     

Synthesis and properties of azoles and their derivatives

Dihydrochlorides of diimino esters of 4,4-dinitropimelic acid are formed from 4,4-dinitropimelic acid dinitrile and alcohols in the presence of hydrogen chloride. The dihydrochloride of the methyl diimino ester condenses with ethylenediamine, o-phenylenediamine, and o-aminophenol to give the corresponding 1,5-bisheteryl-3,3-dinitropentanes.     

Synthesis and properties of azoles and their derivatives

The condensation of 2-trichloromethylbenzimidazole with various N-monosubstituted ethylenediamines has given 1-substitued 2-(benzimidazol-2-yl)imidazolines.     

Synthesis and properties of azoles and their derivatives

The reaction of 4,4-dinitrovaleronitrile with hydrogen chloride and methanol gives the hydrochloride of the methyl imino ester of 4,4-dinitrovaleric acid. The latter is converted to the free imino ester, amide, and methyl ester of 4,4-dinitrovaleric acid. The same hydrochloride readily condenses with ethylenediamine, o-phenylenediamine, or o-aminophenol to give, respectively, imidazoline, benzimidazole, or benzoxazole, which contain a,-dinitrobutyl radical in the 2-position. The methyl imino ester of 4,4-dinitrovaleric acid is rapidly converted to 2,4,6-tris(,-dinitrobutyl)-1,3,5-triazine at room temperature.See [1] for communication V.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 698–699, May, 1971.     

Synthesis of 3-acyl-1-alkyl-2-alkylseleno-1-cyclobutene using alkyneselenolate

The reaction of lithium alkyneselenolate with alpha,beta-unsaturated ketone and then alkyl or acyl halide afforded 3-acyl-1-alkyl-2-alkylseleno-1-cyclobutene. The structure of the cyclobutene was elucidated by IR, MS, (1)H, (13)C, and (77)Se NMR, COSY, HMQC, and HMBC data and X-ray analysis.     

Synthesis of 3,4-diaryl- and 4-acyl-3-arylpyrroles and study of their antimitotic activity

The Barton–Zard reaction of nitro substituted stilbenes and chalcones with ethyl isocyanoacetate afforded 3,4-diaryl- and 4-acyl-3-arylpyrroles, respectively. 3-Arylpyrrole-2,4- dicarboxylates and 4-arylisoxazoline N-oxides were side reaction products. Antimitotic activity of target 3,4-disubstituted pyrroles was studied on a sea urchin embryo model. Pyrroles unsubstituted at positions 2 and 5 were the most active. The activity increased with the number of methoxy groups in the Ar substituent.     

Synthesis of 1-acyl-5-aryl biurets

Fourteen new 1-acyl-5-aryl biurets were synthesized by the reaction of aryl ureas with acylisocynantes. The latter was obtained from acyl chloride and lead cyanate in dichloromethane, using pyridine as catalyst. The structures of compounds 3a-n were confirmed by IR,1H NMR and MS spectra.     

Synthesis and aminomethylation of 6-hydroxyindoles

Condensation of p-benzoquinone with N-aryl--aminocrotonic esters was used to synthesize N-aryl-2-methyl-3-carbethoxy-6-hydroxyindoles, aminomethylation of which gave N-aryl-2-methyl-3-carbethoxy-6-hydroxy-7-dimethylaminomethylindolesTranslated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1354–1356, October, 1973.     

Synthesis and properties of azoles and their derivatives. 35. Synthesis of certain azoles containing sterically hindered phenol residues

The condensation of hydrochlorides of ethyl iminoesters of 4-hydroxy-3,5-di-tert-butylbenzoic and -(4-hydroxy-3,5-di-tert-butylphenyl) propionic acids with monoethanolamine, o-aminophenol, and o-phenylenediamine was studied. As a result, ²-oxazolines, benzoxazoles, and benzimidazoles containing sterically hindered phenol residues in the 2-position were synthesized.For Communication 34, see [1].Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 889–892, July, 1984.     

Synthesis of new azolyl azoles and azinyl azoles

Synthesis of new azolyl azoles and azinyl azoles from the reaction of compounds 1, 4 and 7 with phenyl isothiocyanate is reported. Compound 10 reacts with benzene diazonium chloride to yield either phenylhy‐drazones 11 and 12 or the triazoloquinoline 13 .     

Synthesis of some substituted 3-alkenyl-1-phenylpyrazoles

The regioselective synthesis of new 3-alkenyl-1-phenylpyrazoles 4 from the reaction of phenylhydrazine with 2,3-dihydro-4H-pyran-4-ones 1 is described.     

Synthesis of aromatic 4,4,5,5-tetramethyl-1, 3-dioxolanes substituted in position 2 and their salts

A method for the synthesis of 2-aryl-4,4,5,5-tetrainethyl-1,3-dioxolanium salts from cyclic acetals has been developed. The IR spectra of the compounds obtained are discussed.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 891–893, July, 1973.     

Synthesis and reactivity of substituted α‐carbonylphosphonites and their derivatives

Convenient methods for the synthesis of functionalized organophosphorus compounds containing carbonyl groups as well as di‐ or trialkoxymethyl fragments attached to phosphorus, and their derivatives, starting from the available derivatives of trivalent phosphorus acids, are proposed, and some properties of the new functionalized organophosphorus compounds are presented. So, the alkylation and acylation reaction of (dialkoxymethyl) phosphonites and their analogs have been studied. It is found that the Arbuzov rearrangement of these compounds was accompanied by the phosphorus–carbon bond cleavage with unique retention of the three‐coordinate phosphorus. © 2012 Wiley Periodicals, Inc. Heteroatom Chem 23:352–372, 2012; View this article online at wileyonlinelibrary.com . DOI 10.1002/hc.21024     

Synthesis of substituted [3]dendralenes and their unique cycloaddition reactions

Dimethylsulfonium methylide mediated olefination of 2-phenylethenylidene phosphonoacetate followed by the Horner-Wadsworth-Emmons reaction with aromatic aldehydes provided access to reactive 1,5-diaryl-2-ethoxycarbonyl [3]dendralenes which in situ underwent Diels-Alder cyclodimerisation leading to highly functionalised cyclohexenes with very high regio- and stereoselectivity.