New method for the synthesis of indenes

A new two-step method was developed for the synthesis of 2-sulfonyl-substituted indenes from aromatic aldehydes. The reactions of 1-phenylsulfonyl-1-(trimethylsilyl)ethylene with ortho-lithiated derivatives of aromatic and heteroaromatic aldehydes afford conjugate addition products whose subsequent cyclization gives substituted 2-sulfonylindenes in preparative yields. The reactions of 2-(phenylsulfonyl)indenes with Grignard reagents were studied. It was shown that the sulfonyl group can be replaced in the presence of iron(iii) acetylacetonate.     

New method for the synthesis of tetrathiofulvalene

A new method for the synthesis of tetrathiofulvalene is presented, and conditions for the synthesis of its complex with 7,7,8,8-tetracyanoquinonedimethane are described.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 338–339, March, 1976.     

New method for the synthesis of azolidones

A new method for the synthesis of azolidones by direct condensation of chloroacetic acid and aromatic amines was developed. sym-Dialkylureas are formed in the case of aliphatic amines.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 87–89, January, 1978.     

New method for the synthesis of tetrachlorothiophene

The reaction of tetrachloroethylene with hydrogen sulfide at 450–500 °C leads to the formation of tetrachlorothiophene as the principal product, along with hexachlorobutadiene, the yield of which increases as the reaction temperature is raised. Communication 15 from the series “High-Temperature Organic Synthesis.” See [1] for communication 14. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 310–311, March, 1980.     

New method for the synthesis of macrocyclic compounds

Summary On the basis of transformations carried out witht [10]--cyclothien-1-one it is shown that the higher substituted cycloaliphatic compounds can be prepared from bicyclic compounds containing a thiophene nucleus.Ultraviolet spectra were determined in alcoholic solution with a Hitati (japan) recording spectrophotometer by V. A. Petukhov, whom the authors thank. The Chromatographie analyses were carried out on the Chromatograph designed by the Special Design Office of the Institute of Organic Chemistry by V. I. Yakerson, whom we thank.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya No. 11, pp. 2055–2060, November, 1964     

New method for the synthesis of macrocyclic compounds

Conclusions Results are given which confirm the influence of silica gel on the selectivity of the intramolecular reaction.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 3, pp. 572–576, March, 1968.     

New method for the synthesis of substituted anthranils

Substituted anthranils can be obtained by intramolecular cyclization of o-nitrosoacylbenzenes under the influence of dry hydrogen chloride in an inert solvent. Incorporation of a halogen atom into the 5 or 7 position occurs simultaneously with formation of the anthranil system. Reduction of the anthranils gives difficult-to-obtain o-acylanilines.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1334–1336, October, 1973.     

New method for the synthesis of macrocyclic compounds

The intramolecular acylation of acid chlorides of -(3-methyl-2-thienyl)- and -(4-methyl-2-thienyl)alkanoic acids proceeds at the free 5 position of the thiophene ring. A solid-phase effect (silica gel), which, under comparable conditions, leads to more than double the yields, is displayed during the cyclization of acid chlorides of the above acids. A modification was developed for the reductive desulfurization of cyclothienones with alkyl groups in the position of the thiophene ring; the modification includes the formation of unsaturated compounds and products of the reduction of the carbonyl group. A new route to the synthesis of - and -methylcycloalkanones, including DL-muscone, was developed.See [2] for communication XIII.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 170–176, February, 1972.     

New method for the synthesis of macrocyclic compounds

A method was developed for the preparation of macrocyclic 2-alkylcycloalkanones by alkylation of 2-carbethoxy--cyclothienones with subsequent desulfurization and ketone cleavage. Only C-alkylation occurs under the described conditions (potassium metal in hexamethylphosphoric triamide, sodium hydride in dioxane).See [1] for communication XIV.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 16–21, January, 1973.