Synthesis and Crystal Structure of 2,3-Bis(dinitrofluoromethyl)-1,4-dioxane

For the first time the dinitromethyl group was modified to dinitrofluoromethyl group in the series of aliphatic polynitro compounds in the case of the reaction of 1,1,4,4-tetranitro-2,3-butanediol diacetate with ammonium fluoroxysulfate in the presence of sodium bicarbonate and ethylene glycol. Previously unknown 2,3-bis(dinitrofluoromethyl)-1,4-dioxane was synthesized. Its structure was determined by X-ray diffraction analysis.     

Total synthesis of the racemic alkaloid diptocarpamine

A route for the synthesis of racemic diptocarpamine from hex-5-enoic acid has been developed.Institute of Chemistry, Bashkir Scientific Center of the Urals Branch, USSR Academy of Sciences, Ufa. Institute of the Chemistry of Plant Substances, Uzbek SSR Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 232–236, March–April, 1989.     

Total synthesis of racemic diptocarpidine and diptocarpiline

Convenient methods for the synthesis of racemic diptocarpidine and racemic diptocarpiline have been proposed on the basis of the readily available 6-phthalimidohexyl bromide and hept-6-enoic acid.Institute of Chemistry, Bashkir Branch, Academy of Sciences of the USSR, Ufa. Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 76–82, January–February, 1988.     

Reactions of N- and C-alkenylanilines: VI. Synthesis of 6-methyl-2-[(E or Z)-1-propenyl]anilines and the corresponding anilides and their reaction with bromine

Isomerization of 2-allyl-6-methylaniline by the action of potassium hydroxide at 300°C afforded cis and trans isomers of 2-methyl-6-(1-propenyl)aniline which were converted into the corresponding carbamates by treatment with ethyl chloroformate. Ethyl 2-methyl-6-(1-propenyl)phenylcarbamates reacted with bromine to give mixtures of 4-(1-bromoethyl)-8-methyl-1,4-dihydro-2H-3,1-benzoxazin-2-one and ethyl 2- methyl-6-(1,2-dibromopropyl)phenylcarbamates. Treatment of the same compounds with N-bromosuccinimide resulted in formation of 2-ethoxy-4H-3,1-benzoxazine derivatives. The reaction of N-{6-methyl-2-[(Z)- 1-propenyl]-phenyl}methanesulfonamide gave a mixture of stereoisomeric N-[6-methyl-2- (1,2-dibromopropyl)-phenyl]-methanesulfonamides.__________Translated from Zhurnal Organicheskoi Khimii, Vol. 40, No. 12, 2004, pp. 1815–1818.Original Russian Text Copyright © 2004 by Afonkin, Sotnikov, Gataullin, Spirikhin, Abdrakhmanov.For communication V, see [1].     

Structure of 1-β-d-xylofuranosyluracil in the crystal and in solution

The molecular and crystal structure of 1-β-d-xylofuranosyluracil hydrate was established by X-ray diffraction analysis. The mutual arrangement of the xylofuranose fragment and the nucleic base corresponds to the anti conformation. The furanose ring adopts a C-envelope conformation. The structure of the nucleoside in a DMSO-d₆ solution has been determined by¹H NMR spectroscopy. Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1378–1380, July, 1998.     

Preparation of 4,4a,9,9a-tetrahydrocarbazoles and 1,3a,4,8b-tetra-hydrocyclopenta[b]indoles

Halocyclization of mesylates or tosylates of 2-(cycloalk-2-en-1-yl)anilines gives N-methanesulfonyl-or N-toluenesulfonyl-1-halo-1,2,3,4,4a,9a-hexahydrocarbazoles, heating of which in DMF at 160°C or in piperidine at 110°C leads to 4,4a,9,9a-tetrahydro-3H-carbazoles. Heating N-methanesulfonyl-1-iodo-1,2,3,3a,4,8b-hexahydrocyclopenta[b]indole in DMF at 180—200°C gives 1,3a,4,9b-tetrahydrocyclopenta[b]indole, while in the presence of an ortho-methyl substituent the dehydroiodination reaction proceeds in piperidine at 110°C in high yield. The effect of the nature of the ortho substituent of N-methyl-1-iodo-1,2,3,3a,4,8b-hexahydrocyclopenta[b]indole on the conformational equilibrium of the cyclopentane ring has been established by ¹H NMR spectroscopy. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1184–1190, August, 2006.     

On the emitters of sulfuric acid sonoluminescence

A comparative study of the sonoluminescence spectra of water and argon-saturated aqueous H₂SO₄ solutions was carried out. At an H₂SO₄ concentration of 18 mol L⁻¹, the sulfuric acid sonoluminescence is fifty times more intense than water sonoluminescence. The sulfuric acid luminescence spectrum differs from the water sonoluminescence spectrum caused by the emission of excited water molecules and OH radicals from the gas phase of cavitation bubbles. The sulfuric acid sonoluminescence spectrum exhibits maxima at 330, 420, 500, and 630 nm. Emitters of sonoluminescence of sulfuric acid are the singlet (330–340 nm) and triplet (∼420 nm) excited SO₂ molecules formed by sonolysis of H₂SO₄ molecules. Another product of sonolysis of H₂SO₄, atomic oxygen, is assumed to be responsible for the luminescence at λ = 630 nm. __________ Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1742–1745, August, 2005.     

New type of interaction of 5-iodopyrimidine nucleosides with alkynes

The interaction of 1-(-D-xylofuranosyl)-5-iodo(bromo)uracil derivatives with terminal alkynes in the presence of catalytic amounts of 10% Pd/C and Cul affords the corresponding derivatives of 3-(-D-xylofuranosyl)-6-R-furo[2, 3-d]pyrimidin-2-ones in high yields.Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 596–598, March, 1993.