Regioselective catalytic addition of terminal acetylenes to methyl esters of 1-alkylcyclopropene-3-carboxylic acids

Conclusions Terminal acetylenes and HCN in the presence of CuCl add regioselectively as CH-acids to the unsaturated three-membered ring of methyl esters of 1-alkylcyclopropene-3-carboxylic acids to form the methyl esters of the corresponding 3-alken-5-ynoic acids or 4-cyano-3-alkyl-3-butenoic acids in yields up to 60%.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 10, pp. 2401–2405, October, 1985.These results were partially reported at the Seventh All-Union Conference on the Chemistry of Acetylene [1].     

Vinylcyclopropanation of norbornadiene,norbornene, and dispiroheptadiene by methyl esters of 1-alkylcyclopropene-3-carboxylic acids

Methyl esters of 1-alkylcyclopropene-3-carboxylic acids (I) in the presence of CuCl·P(OPh)₃ cyclopropanate the intracyclic norbornene double bonds of norbornene, norbornadiene, and dispiroheptadiene to give the corresponding vinylcyclopropane adducts in yields up to 80%. 3,5-Dioxo-4-oxatricyclo[5.2.1. 0^2,6]dec-8-ene and 5-acetyl-7-oxabicyclo[2.2.1]hept-2-ene, which are heteroanalogs of dicyclopentadiene and norbornene, are inert relative to (I).Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 1, pp. 214–216, January, 1990.     

Catalytic hydrogenation of methyl esters of some 1h-pyrazoline-3-carboxylic acids

Hydrogenation over Raney nickel of the methyl ester of 1H-pyrazoline-3-carboxylic acid and also of its 4-phenyl and 5-methoxycarbonyl-substituted analogs, leads respectively to 3-aminopyrrolidin-2-one, its 4-phenyl- and 5-methoxycarbonyl derivatives, predominantly to the trans isomer. Under the same conditions 1-amino-4-methoxycarbonylpyrrolidin-2-one was obtained from 3,4-di(methoxycarbonyl)-1H-pyrazoline, but 3,4,5-tri(methoxycarbonyl)-1H-pyrazoline did not react.     

Azides of N-substituted aziridine-2-carboxylic acids. Reaction with methyl esters of amino acids

The corresponding azide was obtained by nitrosation of 1-benzylaziridine-2-carboxylic acid hydrazide. Reaction of the azide with methyl esters of amino acids gave N-(1-benzyl-2-aziridinylcarbonyl)-substituted methyl esters of amino acids.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1350–1352, October, 1980.     

Reaction of methyl esters of substituted 2-oxochromene-3-carboxylic acids with zinc enolates formed from 1-aryl-2-bromoalkanones

Zinc enolates formed from 1-aryl-2-bromoalkanones react with methyl esters of substituted 2-oxochromene-3-carboxylic acids to give methyl esters of 6-bromo- or 6,8-dibromo-4-(2-aryl-2-oxo-1-R- ethyl)-2-oxochromane-3-carboxylic acids as mixtures of two diastereomers.Translated from Zhurnal Obshchei Khimii, Vol. 74, No. 9, 2004, pp. 1520–1523.Original Russian Text Copyright © 2004 by Shchepin, Korzun, Shurov, Vakhrin, Russkikh.This revised version was published online in April 2005 with a corrected cover date.     

3-(1-Aminoalkyl)isoxazole-4-carboxylic acids as peptide bond replacements

An orthogonally protected 3-(1-aminoalkyl)isoxazole-4-carboxylic acid has been prepared by 1,3-dipolar cycloaddition of a suitably protected α-aminonitrile oxide with an enaminoester dipolarophile; this protected amino acid has been deprotected and coupled independently at either the C- or N-terminus to produce pseudopeptide segments as peptide mimetics that contain a cis-amide bond replacement.     

Synthesis of esters of metallocene alcohols and 4,5-dichloroisothiazol-3-carboxylic and 5-arylisoxazole-3-carboxylic acids

Acylation of alkyl- and 1,1′-dialkylferrocene alcohols and diols as well as (3,4,4-trichlorobut-3-ene-1-ol-1-yl)-4,5-cymantrene with dichloroisothiazole- and 5-arylisoxazole-3-carbonyl chlorides has afforded esters containing 1,2-azoles fragments. Some of the obtained compounds have exhibited potentiating action in the binary mixtures with insecticides.     

Study of the reactivities of methyl esters of furan-2-carboxylic and thiophene-2-carboxylic acids by the method of competitive nitration

The reactivities of methyl esters of furan-2-carboxylic and thiophene-2-carboxylic acidswere studied by the method of competitive nitration. Methyl furan-2-carboxylate is more active in its reactions with a mixture of nitric acid and acetic anhydride (with sulfuric acid as the catalyst) and with a mixture of nitric and sulfuric acids (with acetic anhydride as the solvent).Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 601–604, May, 1978.     

Synthesis of esters of substituted 3-aminopyrrole-2-carboxylic acids from thioacrylamides and glycine esters

Morpholides of 3-[(alkoxycarbonylmethyl)amino]thioacrylic acids and esters of 3-morpholinopyrrole-2-carboxylic acids have been obtained from glycine esters and morpholides of 3-hydroxy- and 3-(dimethylamino)thioacrylic acids.Communication 10 of the series Products of the formulation of thioamides; for Communication 9, see [1].Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 628–630, May, 1985.     

Methyl esters of 2-aminotetrahydrobenzothiophene-3-carboxylic acids decorated with trifluoromethyl-containing heterocycles

Russian Chemical Bulletin - Methyl 2-aminothiophene-3-carboxylates were modified with trifluoromethyl-containing five-membered heterocycles by cyclocondensation of methyl trifluoropyruvate...     

Synthesis of methyl esters of 5-aroyl-6-aryl-2-oxo-1,2,3,6-tetra-hydropyrimidine-4-carboxylic acids

Methyl esters of 5-aroyl-6-aryl-2-oxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acids were synthesized from three component mixtures of methyl esters of aroylpyruvic acids, urea, and substituted benzaldehydes. 8-Hydroxy-4,5-diphenyl-3,4-dihydropyrimido[4,5-d]pyridazin-2(1H)-one was synthesized by the reaction of 5-benzoyl-2-oxo-6-phenyl-1,2,3,6-tetrahydropyrimidin-4-carboxylate with hydrazine hydrate.     

Synthesis of methyl esters of 6-dialkylamino-2-(carbethoxy)-methylthiopyrimidine-4-carboxylic acids

A preparative method is proposed for the synthesis of methylesters of 6-dialkylamino-2-(carbethoxy)methylthiopyrimidine-4-carboxylic acids form the butyl ester of orotic acid.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 818–821, June, 1986.