Structure of 3-chloro-6-hydrazinopyridazine in solutions

It is shown by means of the fixed-structure method, UV spectroscopy and dipolemoment method that the product of the reaction of 3,6-dichloropyridazine with hydrazine in solution in methanol and acetonitrile has the 3-chloro-6-hydrazinopyridazine structure.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1536–1539, November, 1982.     

Reactions of 3-acycloxysulfolanes with nucleophilic reagents

In contrast to alkyl esters of carboxylic acids, 3-acyloxysulfolanes on reaction with nucleophilic reagents readily split out a carboxylic acid to give 2-sulfolene, which then reacts with compounds containing a labile hydrogen atom. On the basis of data on the kinetics of alkaline hydrolysis of benzoates, a scheme for elimination of the acid that includes the intermediate formation of a transition state of the E₁CB type is proposed.     

Reactions of 4-chloro-3-formyl-coumarin with primary amines

The reaction of 4-chloro-3-formylcoumarin with primary amines in the presence of triethylamine was studied. The reaction with aliphatic and aromatic amines leads to N-substituted 4-amino-3-formylcoumarins, whereas hetarylamines react primarily with the formyl group to form a mixture of the Z-and E-isomers of N-substituted 3-aminomethylenechroman-2,4-diones. Replacement of the triethylamine by anhydrous sodium acetate in the reaction of chlorocoumarin with 2-aminopyridines leads to the formation of the condensed benzopyranopyridopyrimidine system as a result of nucleophilic attack of the amino group by the chlorine atom at position 4. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 660–668, May, 2006.     

Reactions of 3-hydroxytetrahydropyrimidin-4-ones with electrophilic reagents

The reactions of nonsubstituted or 2-aryl-substituted 3-hydroxytetrahydropyrimidin-4-ones (HTHP) with carboxylic acid chlorides, tosyl chloride, or aryl isocyanates afford mainlyN,O-diacylated,N,O-ditosylated, orN,O-diarylcarbamoylated HTHP, respectively.N,O-Diacylated HTHP are also formed in the reactions of acid chlorides with Schiff's bases based on β-aminopropionohydroxamic acid.N-Acylated HTHP can be obtained by treatingN,O-diacylated HTHP with ammonia. The reactions of 2,2-dialkyl(alkylene)-substituted HTHP with acid chlorides or phenyl isocyanate giveN,O-diacylated orN,O-diphenyl-carbamoylated β-aminopropionohydroxamic acid, respectively. Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2327–2332, December, 1999.     

Reactions of 4-chloro-6-oxo-2,3-dihydro-5-azabenzofurans with amines

The reaction of 7-nitro- and 7-unsubstituted 4-chloro-6-oxo-2,3-dihydro-5-azabenzofurans with primary and secondary amines proceeds with substitution of the chlorine atoms by amine residues and with recyclization of the compounds to 5- and 7-azaindoline derivatives.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No, 10, pp. 1311–1313, October, 1973.We thank Yu. N. Sheinker, E. M. Peresleni, L. M. Alekseeva, N. A. Zosimova, and Yu. I. Pomerantsev for their assistance in conducting the spectral investigations.     

Reactions of nucleophilic substitution of 4-aryl-5-carbomethoxy-6-methyl-2-chloro-3-cyanopyridines

Methods of synthesis of 5-carbomethoxy-substituted pyrazolo[3,4-b]pyridines and 3H-imidazo[4,5-b]pyridines by their reaction with hydrazine hydrate or as a result of Hofmann rearrangement of the corresponding 2-aminopyridines were developed based on 4-aryl-3-carbamoyl(or cyano)-5-carbomethoxy-6-methyl-2-chloropyridines.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No.12, pp. 1646–1650, December 1992.     

Preparation and fungitoxicity of 3-bromo-6-chloro- and 6-bromo-3-chloro-8-quinolinols

Summary 3-Bromo-6-chloro- and 6-bromo-3-chloro-8-nitro, -8-amino-, and -8-hydroxyquinolines along with 3-bromo- and 3-chloroquinolin-6,8-diols were prepared and tested for antifungal activity against six fungi (Aspergillus niger, A. oryzae, Myrothecium verrucaria, Trichoderma viride, Mucor cirinelloides, Trichophyton mentagrophytes) inSabouraud dextrose broth. Compounds with chlorine in the 3 position were generally more fungitoxic than the corresponding analogues with bromine. 6-Bromo-3-chloro-8-quinolinol inhibited four fungi at levels below 1 µg/ml andA. niger andM. cirinelloides at 2 µg/ml each.

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Synthese und Fungitoxizität von 3-Brom-6-chlor- und 6-Brom-3-chlor-8-chinolinolen

Zusammenfassung 3-Brom-6-chlor- und 6-Brom-3-chlor-8-nitro-, -8-amino- und -8-hydroxychinoline sowie 3-Brom- und 3-Chlorchinolin-6,8-diole wurden hergestellt und gegen sechs Pilzstämme (Aspergillus niger, A. oryzae, Myrothecium verrucaria, Trichoderma viride, Mucor cirinelloides, Trichophyton mentagrophytes) inSabouraud-Dextrosenährmedium auf lhre fungizide Aktivität untersucht. Verbindungen mit Chlor in Position 3 sind durchwegs fungitoxischer als die entsprechenden Bromanalogen. 6-Brom-3-chlor-8-chinolinol hemmt das Wachstum von vier Pilzen bei Konzentrationen unter 1 µg/ml und das vonA. niger undM. cirinelloides bei einer Konzentration von jeweils 2 µg/ml.

     

Reactions of methylchlorodisilanes with Grignard reagents

Reactions of Cl₂MeSiSiMeCl₂ with RMgCl make it possible to obtain and isolate pure disilanes containing a smaller number of functional groups, namely, RMeClSiSiMeCl₂ (R = Ph), RMeClSiSiMeRCl (R = Prⁱ, Ph), and R₂MeSiSiMeRCl (R = Buⁱ). The reaction of Cl₂MeSiSiMeCl₂ with BuⁿMgCl is the least selective. The chlorides obtained were reduced with LiAlH₄ into the corresponding hydrides.Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 954–957, May, 1995.     

Reactions of 4-chloro-7-dialkylamino- and 3-alkyl-4-chloro-7-dialkylaminocoumarins with primary and secondary alkylamines

Reaction of series of 4-chloro-7-dialkylaminocoumarins and 3-alkyl-4-chloro-7-dialkylaminocoumarins with primary and secondary amines, namely tert-butylamine, benzylamine, cyclohexylamine, monoethanolamine, diethylamine, piperidine, and morpholine, has yielded novel substituted 4,7-diaminocoumarins. The PMR spectra of these newly synthesized compounds are discussed.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 836–841, June, 1990.     

Reactions of Grignard reagents with 1,3-dicyanoadamantane

Reactions of Grignard reagents RMgX (R = Me, Et, Pr, Bu; X = Br, I) with 1,3-dicyanoadamantane (1) were studied. Optimum conditions for the synthesis of monoaddition products of Grignard reagents to compound 1 were established. The first stage of the reaction of cyanoadamantane 1 with MeMgBr was studied by the MNDO-PM3 method. According to calculations, the more preferable reaction mechanism involves formation of a six-membered cyclic intermediate containing two Mg atoms, two C atoms, and one Br and one N atom.     

Reactions of hexafluorobenzene with some organometallic reagents

The inverse addition of trichloro-2-thienyl-lithium to hexafluorobenzene in THF or ether has given 1,4-bis(trichloro-2-thienyl) tetrafluorobenzene in addition to the tetrakis(trichloro-2-thienyl)difluorobenzene. n-Butyl-lithium with hexafluorobenzene gave mono, bis tris and tetrakis compounds whereas t-BuLi afforded only 1,4-bis(t-butyl)tetrafluorobenzene in excellent yield. Other organolithium and organomagnesium reagents gave the expected products. IR, ¹⁹F NMR and UV spectral data are presented for the several new compounds.     

Reactions of pentafluorophenylgermanium hydrides with Grignard reagents

Dendritic and cross-linked polyphenylenepolygermanes have been obtained by reactions of EtMgBr with (C₆F₅)₃GeH and (C₆F₅)₂GeH₂, respectively. The reaction of sodium naphthalenide with trihydride C₆F₅GeH₃ gives linear insoluble polymer (C₆F₄GeH₂) _n .Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 191–193, January, 1996.     

Reactions of 1-alkoxycarbonylaziridines with nucleophilic reagents

1-Methoxycarbonylaziridines react under mild conditions with a number of nucleophilic reagents such as water, acids, alcohols, and amines with opening of the aziridine ring. In the case of 7-methoxycarbonyl-7-azabicyclo[4.1.0]heptane it was shown by PMR spectroscopy that the ring-opening reaction is realized stereoselectively to give trans-1,2-disubstituted cyclohexanes.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1054–1057, August, 1981.     

Reactions of halonitroacetate esters with amine-type reagents

Conclusions The reactions of halonitroacetate esters with amines, ammonia, and hydrazine yield halonitroacetamides in high yield.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 7, pp. 1572–1575, July, 1986.     

Reactions of substituted phenazine salts with nucleophilic reagents

The condensation of 1-chloro-, 1-phenyl-, 3-chloro-, 3-cyano-, and 3,7-dimethoxy-substituted phenazinium salts with malonic and cyanoacetic esters, N-methylrhodanine, 2-methylbenzothiazolium and quinaldinium salts, aniline, and morpholine was studied. The absorption spectra of the synthesized dyes are described.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1425–1429, October, 1972.