Reactivities of 5-, 6-, and 7-(enamino)indoles in the synthesis of pyrroloquinolines

The concept of regioorientation is proposed for the annelation of the pyridine ring with the participation of 5-, 6-, and 7-aminoindoles. The conclusions based on the experimental data are supported by quantum-chemical calculations.Mordovian State Pedagogical Institute, Sarinks 430007, Russia. Mordovian State University, Sarinsk 430000, Russia. Moscow State University, Moscow 119899, Russia. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1223–1242, September, 1998.     

Stereoselective synthesis of 4-substituted 1,2,3,4,10,10a-hexahydropyrazino[1,2-<Emphasis Type="Italic">a</Emphasis>]indoles

4-Substituted 1,2,3,4-tetrahydropyrazino[1,2-a]indoles were synthesized from 2-cyanoindole. (R)-4-Methyl-1,2,3,4-tetrahydropyrazino[1,2-a]indole was obtained by the Mitsunobu reaction. Stereoselective reduction of 4-substituted 1,2,3,4-tetrahydropyrazino[1,2-a]indoles gave 4-substituted 1,2,3,4,10,10a-hexahydropyrazino[1,2-a]indoles. (4R, 10aR)-4-Methyl-1,2,3,4,10,10a-hexahydropyrazino[1,2-a]indole was synthesized.__________Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 221–225, January, 2005.     

Peculiarities of Mass Spectra of Substituted Pyrroloquinolines

Moscow University Chemistry Bulletin - The results of the mass spectrometric studies of a series of substituted isomeric pyrrolo[2,3-g], [3,2-f], [3,2-g], and [2,3-f]quinolines are presented and...     

Heterocyclic Derivatives of Fullerene C60. 2. Cycloaddition to Fullerene C60 of the Products of Dehydrochlorination of N-Benzyltrifluoroacetimidoyl Chlorides

It has been shown that, depending on the structure, the products of dehydrochlorination of N-benzyltrifluoroacetimidoyl chlorides react with C₆₀ under the action of triethylamine as a [3 + 2] cycloaddition (with the formation of fulleropyrrolines) or a [4 + 2] cycloaddition (with the formation of fulleropiperideines).     

Synthesis of 3-substituted pyrrolidines

A method was developed for the synthesis of derivatives of 3-substituted pyrrolidines from activated alkenes by 1,3-dipolar cycloaddition of unstable 2-benzylazomethylide, generated in situ from N-benzyl-N-(methoxymethyl)-N-(trimethylsilyl)amine. A method was developed for the reduction of 4-(3-pyrrolidyl)pyridine, prepared by the above-mentioned method, to the corresponding derivatives of (3-pyrrolidyl)piperidine with high yields under mild conditions. Dedicated to E. J. Lukevics on his 70th birthday __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 41–48, January, 2007.     

Functionalization of pyridines. 3. Reactions forming a carbon-heteroatom bond with group IV, V, and VI elements

The literature from the last 15–20 years on the synthesis of heteroatomic pyridine derivatives through the formation of pyridine carbon-heteroatom bonds is reviewed. Dedicated to Professor Henk van der Plas on his 70th birthday. For No. 2, see [1]. M. V. Lomonosov Moscow State University, Moscow 119899 Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 437–494, April, 1999.     

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.     

Chirally N-Substituted Indole-2-carbaldehydes. Preparation and Use in Asymmetric Synthesis

A simple method is proposed for the synthesis of optically active indole-2-carbaldehydes via alkylation of 2-cyanoindole by optically active secondary alcohols and subsequent reduction of the cyano group to an aldehyde. Reaction of the aldehydes obtained with aromatic amines gave imines whose reaction with the Danishefsky diene was studied. The structure of the major diastereomer of (2R′)-1-phenyl-2-[1-((1R′)-1-phenylethyl)indol-2-yl]-1,2,3,4-tetrahydropyridine-4-one and minor diastereomer (2S)-2-[1-((1S)-2-methoxy-1-phenylethyl)indol-2-yl]-1-phenyl-1,2,3,4-tetrahydropyridine-4-one respectively were established by X-ray analysis. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1540–1550, October, 2005.