Solid-phase synthesis of 1,2-benzophenazine and some fused imidazole derivatives

The solid-phase synthesis of 1,2-benzophenazine and various N-methylbenzimidazoles using o-diaminoarenes is very promising and permits the synthesis of 1-methyl-4,5-[b]naphtho-1H-imidazole, which could not be obtained by the condensation of o-diaminoarenes with paraformaldehyde using the standard liquid-phase method.M. V. Lomonosov Moscow State University, 119899, Moscow, Institute for Synthetic Polymer Materials, 117461, Moscow, and Institute of Physiologically Active Compounds, Russian Academy of Sciences, Chernogolovka, 1424432, Moscow Oblast. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 672–674, May, 1996. Original article submitted April 3, 1996.     

New approach to the synthesis of dibenzodithia-and benzothiaazacrown ethers via the aromatization of 2-alkylthio(arylthio)cyclohexanes during bromination

A new scheme for the synthesis of dibenzodithiacrown ethers is proposed based on the use of substituted phenol derivatives as intermediates, prepared by aromatization of 2-alkylthio(arylthio)cyclohexanes during bromination. 1,7-Dithia-8,9,17,18-dibenzo-18-crown-6 and 1,10-dithia-11,12,20,21-dibenzo-21-crow-7 without isomers relative to position of the sulfur atoms have been synthesized, and also new thiadiazamacroheterocycles — 1,4,7-trioxa-10,19-dithia-13,16-diaza-12,17-dioxo-8,9,14,15,20,21-tribenzoheneicosane and 1,4,7,10-tetraoxa-13,22-dithia-16,19-diaza-15,20-dioxo-11,12,17,18,23,24-tribenzotetracosane.M. V. Lomonosov Moscow State University, Moscow 119899. M. V. Lomonosov Moscow State Academy for Fine Chemical Technology, Moscow 117571. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 121–127, January, 1997.     

Synthesis of pyrazolo[1,5-a]pyrimidines by the reaction of β-dicarbonyl compounds with 3,5-diamino-4-nitropyrazole

The reaction of 3,5-diamino-4-nitropyrazole with asymmetrical β-dicarbonyl compounds gave polysubstituted pyrazolo[1,5-a]pyrimidines, which are used in reactions with both nucleophilic and electrophilic reagents. The structure of the compounds obtained was demonstrated by x-ray diffraction structural analysis. Center for Pharmacological Chemistry, All-Russian Pharmaceutical Chemistry Institute, 119815 Moscow and M. V. Lomonosov Moscow State University, 119899 Moscow, Russia. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1676–1681, December, 1998.     

Palladium-catalyzed arylation of acrylic acid by diaryliodonium salts in water

M. V. Lomonosov Moscow State University, 119899 Moscow. Translated fromIzvestiya Akademii Nauk, Seriya Khimicheskaya, No. 11, pp. 2685–2686, November, 1992.     

Palladium-catalyzed cross-coupling of diaryliodonium salts with organotin compounds

M. V. Lomonosov Moscow State University, 119899 Moscow. Translated fromIzvestiya Akademii Nauk, Seriya Khimicheskaya, No. 11, pp. 2683–2685, November, 1992.     

Selective binary mobile phase for high-performance liquid chromatography of 12, 13-epoxytrichothec-9-en-8-ones

M. V. Lomonosov Moscow State University. All-Union Scientific-Research Institute of Veterinary Medicine, Moscow. Translated from Khimiya Prirodnykh Soedinenii, Vol. 6, pp. 861–863, November–December, 1989.     

Furocoumarins ofKomarovia anisospermum

Summary Three furocoumarins have been isolated from the roots ofKomarovia anisospermum Korov.: isoimperatorin, phellopterin, and 8-geranyloxy-5-methoxypsoralen. This is the first time that the last-mentioned of these substances has been isolated in the pure state.All-Union Scientific-Research Institute of Medicinal Plants, Moscow. Moscow State University. Botanical Garden, Moscow. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 166–169, March–April, 1976.     

Reactions of sulfur dichloride with allylthienyl sulfides

The reaction. of allyl-2-thienyl sulfide with sulfur dichloride yields products of intermolecular- addition of intermediately formed sulfenyl chloride to the starting sulfide, and in the case of allyl-3-thienyl sulfide, intramolecular cyclization also takes place with formation of a compound of the thienodithiin series.Moscow State University, Chemistry Faculty, Moscow 119899. A. N. Nesmeyanov Institute of Organometallic Compounds, Russian Academy of Sciences, Moscow 117813. Translated Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 767–769, June, 1994. Original article submitted April 18, 1994.     

Microbiological transformations of 9-amino-1,2,3,4,5,6,7,8-octahydroacridine

Chemistry Faculty, M. V. Lomonosov Moscow State University, Moscow 199899. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 712–713, May, 1994. Original article submitted April 25, 1994     

Reaction of i-acetyl-2-phenyl-5-hydroxypyrazolidines with alcohols on the surface of adsorbents

A novel method for synthesis of 5-alkoxypyrazolidines on the surface of an adsorbent allows us to obtain derivatives of allyl, tertiary, and chiral alcohols.M. V. Lomonosov Moscow State University, Moscow 119899. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp 1489–1493, November, 1995.     

Microbiological synthesis of 4-hydroxy-5-isopropyl-5-methoxy-2-oxo-2,5-dihydrofuran

M. V. Lomonosov Moscow State University, Moscow 119899, and Chemistry Section, Leipzig University, 7062 Leipzig, Germany. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 711–712, May, 1994.     

Synthesis of certain dipyridylacetylenes using palladium-catalyzed cross-coupling of ethynyl-and halopyridines

A series of dipyridylacetylenes were obtained by reacting ethynypyridines with chloro- and bromopyridines during catalysis with phosphino complexes of palladium in the presence of copper iodide and a base.M. V. Lomonosov Moscow State University, Moscow 119899. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, 1378–1383, October 1994. Original article submitted November 22, 1994.     

Some reactions of 8,11,11-trimethyl-11-silabenzo[b]naphtho-[2,3-d]thiophen-6-one at the carbonyl group

Reactions of C- and N-nucleophiles at the carbonyl group of 8,11,11-trimethyl-11-silabenzo-[b]naphtho[2,3-d]thiophen-6-one have been studied. PMR Spectroscopy showed that condensation with aniline gives a mixture of the Z- and E- isomers of the corresponding azomethine. Reaction with n-butyl and phenyllithium gave tertiary alcohols, the molecular structure of which was proved using X-ray crystallography.State Science Research Institute for Chemical Reagents and High Purity Chemical Substances, Moscow 107076, Russia. Russian Peoples Friendship University, Moscow 117198. N. D. Zelinskii Institute of Organic Chemistry, Russian Academy of Sciences, Moscow 117913, Russia. M. V. Lomonosova State University, Moscow 119899, Russia. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 829–835, June, 1999.     

Quantum-chemical analysis of the conformational and diastereomeric composition of 1,3-dimethyl-4-(s-phenylethylimino)piperidine

The serniempirical quantum-chemical methods MNDO, AMI, and PM3 are used in a complete conformational analysis of 1,3-dimethyl-4-(S-phenylethylimino)piperidine.M. V. Lomonosov Moscow State University, Moscow, 119899. Translated from Khimiya Geterotsiklicheskikh Soedinenii. No. 3, pp. 359–360, March, 1996.     

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.     

Synthesis of halogenopyridines (review)

Published data on the synthesis of derivatives of pyridines containing halogen atoms directly at the carbon atoms of the pyridine ring are reviewed.Moscow State Textile Academy, Moscow 117918. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1155–1187, September, 1996. Original article submitted July 6, 1994.     

Synthesis of trifluoromethyl derivatives of pyrazolidine- and 2-pyrazoline-1-carboxamides and pyrazolidine- and 1-pyrazoline-carbothioamides

The reactions of enones containing trifluoromethyl groups with semicarbazide in basic media proceed unequivocally to give pyrazolidine-1-carboxamides. The direction of the reactions of these enones with thiosemicarbazide depends on their structure; the reaction products are pyrazolidine- and 2-pyrazoline-1-carbothioamides. An enone containing a CF₃ group and an ethoxy group capable of replacement reacts with semicarbazide to give 2-pyrazoline-1-carboxamide and with thiosemicarbazide to give the double addition product, 5-(1-thiosemicarbazido)-2-pyrazoline-1-carbothiamide.M. V. Lomonosov Moscow State University, 119899 Moscow, Russia, N. S. Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, 117907 Moscow, Russia. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 634–644, May, 1998.     

Once again the question of cyclization of pyrazolones-5 unsubstituted at the nitrogen into tripyrazolynenes

The experimental data were refined and the yields were improved significantly in cyclization of pyrazolones-5 into tripyrazolylenes-1,5 with phosphorus oxychloride.K. A. Timiryazev Moscow Agricultural Academy, Moscow 127550, Russia. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 704–705, May, 1998.     

Homolytic ethoxycarbonylation of 3-nitropyridines

The homolytic ethoxycarbonylation of alkyl-3-nitropyridines has been accomplished for the first time by the action of ethyl pyruvate and hydrogen peroxide in the presence of ferrous sulfate. M. V. Lomonosov Moscow State University, 119899 Moscow. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1502–1503, November, 1997.     

Advanced in the synthesis of heterocyclic compounds from aliphatic nitro derivatives. A review

The literature on the synthesis of heterocyclic compounds from aliphatic nitro derivatives in the past decade has been summarized.Moscow State Textile Academy, 117918, Moscow. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1299–1336, October, 1994. Original article submitted October 6, 1994.