Tandem cleavage of 2,3,5-trimethyl 7-trifluoroacetyl-1,2,3,4-tetrahydro-pyrrolo[1,2-<Emphasis Type="Italic">c</Emphasis>]pyrimidine by activated alkynes,caused by Michael addition of a tertiary nitrogen atom to a triple bond

The interaction of 7-trifluoroacetyltetrahydropyrrolo[1,2-c]pyrimidine with acetylenedicarboxylic ester (DMAD) and ethyl propiolate in acetonitrile and alcohols has been studied. It was established that DMAD splits pyrrolopyrimidine at the aminal fragment in acetonitrile and methanol with the formation of 1-H-and 2-(N-dimethoxycarbonylvinyl-N-methyl)aminoethyl-1-methoxymethyl-3-methyl-5-trifluoroacetylpyrroles. In acetonitrile ethyl propiolate splits pyrrolopyrimidine both at the aminal fragment and at the C₍₃₎-N₍₂₎ bond (Hofmann reaction), but in ethanol only at the C₍₃₎-N₍₂₎ bond with the formation of 2-propenylpyrroles. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 1082–1087, July, 2007.     

Tandem transformations of tetrahydropyrrolo[3,2-<Emphasis Type="Italic">c</Emphasis>]pyridines under the action of dimethyl acetylenedicarboxylate. A novel route to pyrrolo[2,3-<Emphasis Type="Italic">d</Emphasis>]azocines

Reactions of substituted tetrahydropyrrolo[3,2-c]pyridines with dimethyl acetylenedicarboxylate in protic and aprotic solvents were studied. A novel single-step method for the synthesis of pyrrolo[2,3-d]azocine derivatives was developed. Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2513–2519, November, 2005.     

Synthesis of hexahydroazonino[5,6-b]indoles from hexahydroazepino[4,3-b]-and-[3,4-b]indoles and activated alkynes

A reaction of substituted hexahydroazepino[4,3-b]-and-[3,4-b]indoles with activated alkynes was studied. A one-step method for the synthesis of isomeric hexahydroazonino[5,6-b]indoles different by positions of the double bond in the azonine ring was developed. Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2244–2250, November, 2007.     

Synthesis of tetrazolodiazepines by a five-centered four-component azide Ugi reaction. Scope and limitations

Tetrazolo[1,5-a][1,4]benzodiazepines were obtained by an efficient azide five-centered four-component Ugi reaction, which used ketones, sodium azide, ammonium chloride, and the corresponding isonitrile. Scope and limitations of this multi-component reaction were considered.     

Synthesis of 3,4-dihydroisoquinolines using nitroalkanes in polyphosphoric acid

Russian Chemical Bulletin - A new method for the synthesis of 6,7-dimethoxy-3,4-dihydroisoquinoline based on the reaction of 2-(3,4-dimethoxyphenyl)ethan-1-amine (homoveratrylamine) with aliphatic...     

The first synthesis of tetrahydrobenzo[b]pyrrolo[2,1-f][1,6]naphthyridine by the Michael addition of butyn-2-one to 1-(2-methoxycarbonylvinyl)tetrahydrobenzo[b][1,6]naphthyridine

Russian Chemical Bulletin -