Reaction of acridine with pyrazolone derivatives

A mixture of acridine and a pyrazolone derivative was reacted in the solid state (without solvent). It is proposed that the enol tautomer (the C4‐position) of the pyrazolone derivative attacks the C9‐position of acridine through a nucleophilic reaction resulting in products where the C4‐position of pyrazolone is connected to the C9‐position of acridine. When the reaction of 3‐methyl‐1‐phenyl‐5‐pyrazolone and acridine was carried out at low temperature (25°–50°), the reaction product was obtained even when the majority of the reaction mixture had not melted. The same reaction was also carried out in the presence of an ultrasonic wave at same temperature (25°–50°) and the reaction product was obtained in high yield. Under ultrasonic conditions, the reaction mixture was not melted. However, the interface between 3‐methyl‐1‐phenyl‐5‐pyrazolone and acridine gradually changed from white to black. In this reaction, the dihydroacridine dimer is not obtained.     

Reaction of dichloronitrobenzofuroxanes with amines and their derivatives

Reactions of 4,6-dichloro-5,7-dinitrobenzofuroxane and 4,6-dichloro-5-nitrobenzofuroxane with some aliphatic amines were studied. In the reaction of 4,6-dichloro-5,7-dinitrobenzofuroxane with 2,2-dimetoxyethylmethylamine the monosubstituted product was formed for the first time. In the reactions of 4,6-dichloro-5-nitrobenzofuroxane with amines substitution only of one chlorine atom takes place.     

Reaction of diaroylethylenes with ortho-phenylenediamine and its derivatives

Derivatives of 1,2-dihydroquinoxaline were synthesized. The direction of the reaction of unsymmetrical diaroylethylenes with o-phenylenediamine was shown by chemical and spectral methods and the reaction mechanism was discussed.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5 pp. 656–661, May, 1986.     

Reaction of carboryne with styrene and its derivatives

Reaction of carboryne generated from 1-I-2-Li-1,2-C₂B₁₀H₁₀ with styrene and its derivatives has been studied. In addition to [2+2] cycloaddition reaction and/or ene reaction, an extra-annular [4+2] cycloaddition reaction is also observed, depending upon the substituents on the vinyl unit. The resulting [4+2] cycloaddition intermediates are so reactive that they immediately undergo rearomatization via either a formal 1,3-hydrogen rearrangement or dehydrogenation initiated by hydrogen abstraction with carboryne in biradical form, to give 3,4-dihydronaphtho[1,2]-o-carboranes and naphtho[1,2]-o-carboranes, respectively. In sharp contrast to that of benzyne, further additions of carboryne onto the primary cycloadducts are not observed.     

The He-I photoelectron spectra of uranocene and thorocene

The bonding in unranocene and thorocene is discussed in the light of their photoelectron spectra and ionization of 5f electrons is identified.     

Reaction of trimethyliodosilane with monosubstituted acetylene derivatives

Conclusions The reaction of phenylacetylene and 1-hexyne with Me₃SiI in the presence of Mg at 170–180° gave the corresponding trimethyl(organylethynyl)silanes in 80–95% yield.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 4, p. 897, April, 1981.     

Reaction of trifluoromethyl-containing enones with thiophenol derivatives

The reaction of trifluoromethyl-containing enones with thiophenol derivatives has been studied. Reactions with 4-methylthiophenol proceed with the formation of either ketosulfides or a pyran derivative. Reactions of trifluoromethyl-containing enones with 2-mercaptobenzaldehyde lead to 3-trifluoroacetyl-substituted 2H-thiochromenes. M. V. Lomonosov Moscow State University, Moscow 119899, Russia N. S. Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, Moscow 117907, Russia. Department of Chemistry, University of Durham, South Road, Durham, Great Britain, DH1 3LE. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 618–626, May, 1999.     

Reaction of ethyl quininate derivatives with phenyllithium

The reactions of ethyl quininate and its 1-methyl-2-oxo derivative and ethyl 1-methyl-1,2,3,4-tetrahydroquininate with phenyllithium were investigated. The structures of the products were confirmed by IR, PMR, and mass-spectroscopic data.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 368–373, March, 1978.     

Reaction of arylhydrazines with α-formylbutyrolactam derivatives

The Vilsmeier formylation of butyrolactam and of N-phenylbutyrolactam has given their -dimethylaminomethylene derivatives. The reaction of the latter with -substituted arylhydrazines leads to the formation of 1-oxo-1,2,3,4-tetrahydro--carbolines. When unsubstituted phenylhydrazine is used, the occurrence of a competing reaction leading to -aminoethyl derivatives of 5-pyrazolone is also possible. It has been established that the direction of the reaction and the ratio of the products are affected by the substituent at the lactam nitrogen atom.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 56–60, January 1984.     

Reaction of isoquinolinium methylide derivatives with trimethylsilylketene

Our investigation on the reaction of isoquinolinium methylide derivatives with trimethylsilylketene (TMS ketene), giving [3+2] cycloadducts, pyrroloisoquinolines, is described. TMS ketene is found to function as the C2 unit introducing reagent in the reaction of isoquinolinium methylide derivatives. Furthermore, the advantage of TMS ketene in comparison with ketene (CH₂CO) is shown.     

Reaction of epoxypropylcarbazole derivatives with 2-phenylindole

The reactions of 9-(2,3-epoxypropyl)carbazole and the glycidyl ether of 1,3-di(9-carbazolyl)-2-propanol with 2-phenylindole were studied. The addition of the epoxypropylcarbazole derivatives to 2-phenylindole in 2-butanone in the presence of alkali at room temperature occurs at the nitrogen atom, while the addition proceeds at C₍₃₎ upon heating these epoxy compounds with 2-phenylindole.Kaunas Technological University, Kaunas LT-3028, Lithuania. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 898–902, July, 2000.     

Reaction of dimethyl sulfite with dimethylaminomethyl derivatives

Conclusions The reaction of dimethylaminomethyl derivatives Me₂NCH₂X with dimethyl sulfite proceeds by analogy with the Arbuzov rearrangement under mild conditions. The yield of the rearrangement product increases with increasing nueleophilicity of (X).Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No.1, pp. 220–223, January, 1986.     

Reaction of furan derivatives with acryloyl chloride

Summary 2-Methyl-, 2-(2'-carbomethoxyethyl-, 2-(3'-oxobutyl)-, and 2-(3',3'-dimethoxypropyl)furans add acryloyl chloride to yield furan acid chlorides or substituted furancarboxylic acids, which with alcohols form the corresponding esters.     

Reaction of mercaptopyrimidine derivatives with perfluoro olefins

The reaction of methyl and hydroxy derivatives of 2- and 4-mercaptopyrimidines with perfluoropropylene and perfluoro-1-hexene was investigated. The corresponding perfluoroalkenylthio-substituted pyrimidines are described.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 402–406, March, 1984.     

Reaction of isonitriles with perfluoromethacrylic acid derivatives

Conclusions The amide and ester of perfluoromethacrylic acid easily add isonitriles to give the 1,4-cycloaddition adducts.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 8, pp. 1898–1899, August, 1975.     

Reaction of acyl isocyanates with pyridine derivatives

Conclusions Trichloroacetyl isocyanate reacts with 2- and 4-picolines to form substituted trichloroacetylamidates. Benzoyl isocyanate forms a dimer in the presence of picolines. Depending on the nature of the solvent, trichloroacetyl isocyanate adds to 4-vinylp'yridine either at the vinyl group or at the ring nitrogen atom.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 9, pp. 2127–2130, September, 1984.