Synthesis of substituted 3-aminospiro-4-but-2-enolides

Previously unknown 3-N-alkylamino-, 3-N,N-dialkylamino-4-but-2-enolides containing spirocyclic moiety have been synthesized by nucleophilic addition of amines at the triple bond of methyl ester of β-(1-hydroxycyclohexyl)propiolic acid or by the reaction of amines with the corresponding 3-methoxy-4-but-2-enolide. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow 117913, Russia. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1330–1335, October, 1999.     

Reaction of 4-ethoxychromylium salts with some amines

The reactions of 4-ethoxychromylium salts with some amines were studied. It was shown that o-hydroxyarylpyrazoles and chromone phenylhydrazones, respectively, are formed by the reaction of these salts with hydrazine and phenylhydrazine. The action of primary aromatic amines leads to replacement of the 4-ethoxy group by a 4-arylamino group, while the reaction of the 4-ethoxychromylium salts with N,N-diethylaniline gives 4-ethoxy-4-diethylaminoflavylium salts.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1112–1114, August, 1971.     

Reaction of methyl trifluoropyruvate with aryl amines

Conclusions We have found a novel reaction of primary and some secondary aryl amines with methyl trifluoropyruvate, which yields derivatives of 3-hydroxy-2-oxo-3-trifluoromethylindoline.For preliminary communication, see [1].Translated from Izvestiya Akademii-Nauk SSSR, Seriya Khimicheskaya, No. 9, pp. 2080–2085, September, 1986.     

Reaction of some benzoxazoline-2-thione derivatives with amines

Hydroxyphenylthioureas were obtained by the reaction of nitro, chloro, bromo, or amino derivatives of benzoxazoline-2-thiones with primary amines. If the substituent in the benzene ring is a nitro group, the reaction with certain secondary amines proceeds with the production of trisubstituted thioureas. It is shown that electron-acceptor substituents in the 5 and 6 positions of the benzene ring facilitate this reaction.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 180–181, February, 1981.The authors thank P. Braikov, I. Nachev, I. Dukhova, and T. Georgiev for their assistance in carrying out some of the experiments.     

Reaction of N-phenylsulfonylbenzoxazolone with some amines

The reaction of N-phenylsulfonylbenzoxazolone with amines was investigated in order to study the mechanism of the reaction between aryloxazolones and amines. The sulfonyl group accelerates the reaction considerably. The structure of 2-(phenylsulfamido)phenyl esters of the corresponding N-substituted carbamic acids was assigned to the products on the basis of the IR spectra and alternative synthesis. The reaction with secondary aliphatic amines (dimethyl- and diethylamine)proceeds considerably more slowly and results in the formation of 2-(phenylsulfamido)phenol.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1333–1336, October, 1971.     

Reaction of some sympathomimetic amines with sodium 1,2-naphthoquinone-4-sulphonate

Summary The condensation products of 4 sympathomimetic amines with 1,2-naphthoquinone-4-sulphonic acid have been prepared and examined. A spectrophotometric procedure based on the chloroform-soluble orange-red condensation product is described. The same products were investigated fluorimetrically after reduction with sodium borohydride. The results obtained are satisfactory.

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Zusammenfassung Die Kondensationsprodukte vier sympathicomimetischer Amine mit 1,2-Naphthochinon-4-sulfonsäure wurden dargestellt und untersucht. Ein spektralphotometrisches Verfahren auf der Grundlage des chloroformlöslichen, orangeroten Kondensationsproduktes wurde beschrieben. Die gleichen Produkte wurden auch fluoreszenzanalytisch nach ihrer Reduktion mit Natriumborhydrid untersucht. Die Ergebnisse sind befriedigend.

     

Reaction of γ-nitroketones and methyl 4-nitrobutanoates with formaldehyde and primary amines

5-Nitropentan-2-one reacts with methylamine and formaldehyde according to the Mannich reaction pattern to give 5-hexahydropyrimidinylcarbonyl-substituted 1-nitro-3,7-diazabicyclo[3.3.1]nonane in one experimental stage. When methyl 3-R-4-nitrobutanoates are used, the reaction stops after the formation of substituted 5-nitrohexahydropyrimidines in 40–98% yields. Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1687–1693, July, 2005.     

Reaction of some amines with unsaturated N-acylbenzoxazolones

It is shown that the addition of aniline proceeds at the carbon-carbon double bond of N-acryloyl-, N-chloroacryloyl-, and N-methylacryloylbenzoxazolones. The basicity of the amine has a substantial effect on the course of the reaction with various amines. Transamidation of the acryloyl residue occurs with strongly basic amines.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1044–1048, August, 1974.     

Synthesis and some properties of substituted 4-azafluorenes

Some chemical properties — the oxidation, condensation with aromatic aldehydes, bromination, dimerization, and amination — of 4-azafluorenes derived from -methylene-1,5-diketones are studied.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 950–953, July, 1990.     

Synthesis of some novel 2-thioxoimidazolidin-4-one substituted glycosyl hydrazone derivatives

Russian Journal of General Chemistry - A series of novel 2-thioxoimidazolidine glycosides were prepared via reaction of the key intermediate...     

Reaction of substituted chalcones with methyl 1-bromocycloalkanecarboxylates and zinc

Methyl 1-bromocyclopentane-and 1-bromocyclobutanecarboxylates react with zinc and substituted chalcones to form spiro-3,4-dihydropyran-2-one derivatives: 8, 10-diaryl-7-oxaspiro[4.5]dec-8-en-6-ones and 7,9-diaryl-6-oxaspiro[3.5]non-7-en-5-ones, respectively.     

Synthesis of some 3-functionally substituted 2-pyrazolines

Reaction of the complex of 1-phenyl-3-pyrazolidone and phosphorus oxychloride with nucleophilic agents (amines and thiophenol) leads to the formation of 3-functionally substituted 2-pyrazolines.M. V. Lomonosov Moscow State University, Moscow, 119899. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp, 1494–1498, November, 1995. Original article submitted September 18, 1995.     

Synthesis of some substituted 1-(2-propynyl)-4-piperidones

Summary Some 1-(1,2-dimethyl-2-propynyl)-4-piperidones were synthesized, and the effect of substitution in the piperidine ring on the reversible cyclization of unsaturated-alkylamino ketones into 4-piperidones was investigated.     

Reaction of some coumarin and 4,6-diaryl-2H-pyran derivatives with secondary amines

The reaction of piperidine, morpholine, piperazine or dimethylamine with several coumarins, 3-bromocoumarin, 4,6-diaryl-2H-pyran-2-ones and 3-bromo-4,6-diaryl-2H-thiopyran-2-ones gave o-hydroxycinnamic acid amides, benzofurans, open-chain δ-oxoamides and thiophene derivatives, respectively.     

Synthesis of methyl 2-aryl-5-chlorosulfonyl-1,3-oxazole-4-carboxylates and their reactions with amines and amidines

Previously unknown methyl 2-aryl-5-chlorosulfonyl-1,3-oxazole-4-carboxylates have been synthesized. Their reactions with amines and amidines have yielded the corresponding sulfonamides and 6H,7H-[1,3]oxazolo-[5,4-d]pyrimidin-7-ones.     

Reaction of carbamoyl derivatives of 4- and 5-hydroxyl-aminothiazolidine-2-thiones and 4-hydroxylaminoimid-azolidin-2-one with methyl chloroformate. Properties of substituted 1,2,4-oxadiazolidine-3,5-diones

Acylation with methyl chloroformate of N-monocarbamoyl derivatives of 4- and 5-hydroxylaminothiazolidin-2-thione and 4-hydroxylaminoimidazolidin-2-one, depending on their structure and the reaction conditions, leads either to N,O-bisacylhydroxylamines or to their intramolecular cyclization products, the substituted 1,2,4-oxadiazolidine-3,5-diones which, on decarboxylation, may convert into the corresponding 4- and 5-carbamoyliminothiazolidine-2-thiones.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 984–989, July, 1990.