New derivatives of 4-quinaldinol

The reactions of 1, 1, 3-trichloro-1-propene and also 1, 1, 1-trichloro-2-propene with acetoacetic ester gave α-(γ, γ-dichlorallyl)acetoacetic ester (I). In the reactions with aniline and o- and p-toluidines, the corresponding α-(γ, γ-dichloroallyl)-β-arylamino-crotonic esters were produced, thermal cyclization of which gave 2-methyl-3-(γ, γ-dichloroallyl)-4-hydroxyquinoline (II) and its 6CH₃- (III) and 8CH₃- (IV) homologs. With phosphorus oxychloride, II–IV gave the corresponding 4-chloro-substituted quinolines (V–VII); with concentrated sulfuric acid, II–VII were converted into the corresponding β-quinolinylpropionic acids VIII–XIII.     

New 4-quinaldinol derivatives XVII. 2-Methyl-3-(3-chloro-2-buten-1-yl)-4-hydroxyquinoline-6-carboxylic acid and some of its transformations

1-(2-Methyl-4-hydroxy-6-carboxy-3-quinolinyl)-3-butanone and 1-(2-methyl-4-chloro-6-carboxy-3-quinolinyl)-3-butanone were obtained by the acid hydrolysis of 2-methyl-3-(3-chloro-2-buten-1-yl)-4-hydroxy(chloro)quinoline-6-carboxylic acids and their esters.See [6] for communication XVI.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1681–1682, December, 1971.     

New derivatives of quinaldin-4-ol

The synthesis and chemical reactions of 3-(3,3-dichloroallyl)-4-hydroxy-2-methylquinoline-6-carboxylic acid, 3-(2-carboxyethyl)-4-hydroxy-2-methylquinoline-6-carboxylic acid, and of derivatives of these acids are described.For Communication XVIII, see [1].Translated from Khimiya Geterotsiklicheskikh Soedinenii, Vol. 6, No. 7, pp. 966–968, July, 1970.     

异苯并二氢吡喃衍生物新合成方法的研究

用新方法合成了一系列异苯并二氢吡喃衍生物。其特点是产率高, 反应时间短, 成本低, 污染小。所合成的异色满麝香均经元素分析, 红外光谱和核磁共振谱予以证实。     

New synthesis of 3-methoxy-4-substituted pyrazole derivatives

A simple and efficient protocol for the synthesis of 3-methoxy-4-arylmethylene- and 3-methoxy-4-heteroarylmethylenepyrazoles has been developed. These derivatives are obtained in one step from alcohols 3 or 8a-b.     

New substituted 4-azatricyclo[4.3.1.13,8]undecane derivatives

The synthesis of a series of new substituted 4-azatricyclo[4.3.1.1^3.8]undecane and 4-azatricyclo[4.3.1.1^3.8]-undecan-5-one derivatives is described. Compounds 4f and 4g displayed antiviral activity.     

New 4(5H)-oxazolonium perchlorate derivatives

The condensation of 2,3-dimethyl-4(5H)-oxazolonium salts with ethyl orthoformate and amides of 5-substituted 2-furancarboxylic acids gives the corresponding products derived by modification of the methyl group at C₍₂₎, 2-formylmethylene-4-oxazolidinone and 2-furoylaminoethenyl-4(5H)-oxazolanium perchlorates.Kuban State Technological University, 350072, Krasnodar. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 236–237, February, 1995. Original article submitted September 30, 1994.     

New route to N-aryl and N-heteroaryl derivatives of 4-hydroxy-3-quinolinecarboxamides

The synthesis of N-aryl and N-heteroaryl substituted 4-hydroxy-3-quinolinecarboxamides 1 is described. The attack of dianions 12 of N-aryl substituted acetamides on the C-4 carbonyl of 4H-3,1-benzoxazin-4-ones 11 gave rise to ketoamides 13 , which smoothly cyclised in the presence of bases to afford quinolinecarboxamides 1 . By this method, a large number of 2-substituted 4-hydroxyquinolinecarboxamides can be prepared.     

4-Formylsydnonimine derivatives

The procedure for the synthesis of 4-formylsydnonimine derivatives based on the reaction of 4-lithiosydnonimines with (methoxymethylidene)dimethylammonium methyl sulfate was proposed.     

New isatin derivatives

The review compiles published data on the synthesis and biological action of new isatin derivatives containing in their composition additional oxygen, nitrogen, or sulfur heterocycles.     

New derivatives of N-nitrosamines

Two new derivatives are proposed for determination of nitrosamines by GLC. One is formed by reaction with di(2-chloroethyl) phosphochloridate and the other by reaction with m-trifluorotoluene sulphonyl chloride.     

New 4-(benzotriazol-1-yl)-1,2,3-triazole derivatives

A new 4-(benzotriazol-1-yl)-1,2,3-triazole structure was obtained by the diazotization reaction of either of 1-(2-aminophenyl)-4-carboxamido-5-amino-1H-1,2,3-triazole ( 1c ) or of the corresponding Dimroth isomer 1d . It underwent some common reactions to evaluate its chemical behaviour and structure. An analogous reaction sequence was carried out from the 2-nitro-4-methylphenyl azide, to assign the structure to the nitro derivatives prepared. The structure of the new compounds prepared was confirmed by chemical and spectroscopic methods.     

New derivatives of meso-(tetra-4-pyridyl)porphine and their reactions

Some reactions of Co-meso(tetra-4-pyridyl)porphine were carried out, and a cyanopyridine complex was isolated. New water-soluble complexes based on Co-meso-(tetra-4-N-hydroxyethylpyridyl)porphine were obtained. Aliphatic, aromatic, and heterocyclic amines were examined as ligands.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 212–216, February, 1986.     

New 4-pentafluorosulfanyl and 4-perfluoroalkylthio derivatives of 1-chloro-2-nitro- and 1-chloro-2,6-dinitrobenzenes

New 4-pentafluorosulfanyl and 4-perfluoroalkylthio derivatives of 1-chloro-2-nitrobenzene and 1-chloro-2,6-dinitrobenzene were prepared from the corresponding bis(4-chloro-3-nitrophenyl)disulfide and bis(4-chloro-3,5-dinitrophenyl)disulfide, respectively. The SF₅ derivatives were obtained by fluorination of the disulfides with AgF₂ according to Sheppard’s method, while perfluoroalkylation was carried out by means of thermolytic reactions with xenon(II) bis(perfluoroalkylcarboxylates). The introduction of fluorine-containing, electron-withdrawing substituents into the aromatic ring (in the presence of other deactivating groups) reinforces the activation of the halogen substituent towards nucleophilic attack. Several nucleophilic substitution reactions have been carried out with these compounds, and as a result, some N- and S-containing groups were introduced in the benzene ring. For example, the previously unknown SF₅, CF₃S, and C₂F₅S analogues of trifluralin (Treflan^®) were prepared and characterized. Additional synthetic possibilities for heterocyclic chemistry are presented on the basis of reactions of the new 1-chloro-2,6-dinitrobenzene derivatives with ethyl thioglycolate wherein fluorine-containing derivatives of benzothiazole N-oxide were obtained as the main products.     

Some derivatives of 4-fluorobenzenethiol

Various metallic and organometallic derivatives of 4-fluorobenzenethiol have been prepared directly from the thiol. Its Ag(I), Ni(II) and Pb(II) salts were used to synthesize thioethers thioesters. New compounds have been characterized by elemental analysis, NMR (H-1, F-19 and C-13) and mass spectroscopy.     

Synthesis of 4-thiouridine derivatives

The thionation of a protected uridine with the aid of P₂S₅ has given the corresponding 4-thiouridine derivatives, which have been phosphorylated at the 5 or the 2(3)hydroxyl. On being heated in aqueous pyridine solution with liquid hydrogen sulfide, cytidine phosphates also form 4-thiouridine phosphates. 4-Thiouridine 2,3-cyclophosphate has been obtained.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 996–1000, July, 1973.The authors thank M. Ya. Karpeiskii for his constant interest in the work and for valuable critical observations.     

New 2-methylbenzimidazole derivatives

New 2-methylbenzimidazole derivatives with a methyl, ethyl, or phenyl group at position 1, and a hydroxymethyl, aldehyde, or ß-carboxyl group at position 5 are synthesized. Imidocyanine dyes with aldehyde and ß-carboxyl groups in the heterocyclic portions are obtained, and their main light absorption maxima determined.