A. N. Levov

Heterocyclization of tropinone oximes and 3-methyl-3-azabicyclo[3.3.1.]-nonan-9-one with acetylene in a superbasic medium

Tropinone oxime reacts with acetylene in syperbasic medium to form ordinary products of heterocyclization. The oxime of 3-methyl-3-azabicyclo[3.3.1]nonan-9-one does not undergo heterocyclization due to the impossibility of a [3,3]-sigmatropic rearrangement of its vinyl ether.

Conversion of 3-benzoyl-1-methyl-4-phenyl-γ-piperidol by arylamines and arylhydrazines. Synthesis of 3-arylamino-1-oxo-1-phenylpropanes and 1,3-diarylpyrazoles and their fragmentation under electron impact

It has been established that on heating, 3-benzoyl-4-hydroxy-1-methyl-4-phenylpiperidine is ring-opened in the presence of arylamines by a type of retroaldol reaction, with subsequent transamination of the intermediate Mannich base and the formation of 3-arylamino-1-oxo-1-phenylpropanes. When using arylhydrazines this γ-piperidol is recyclized with the formation of 1,3-diarylpyrazoles and their 4,5-dihydro derivatives. The mass spectral behavior of a series of 3-arylamino-substituted 1-phenylpropanones has been studied.

Synthesis of Substituted and Condensed Tetrahydrospiro[benzo-2-azepinecyclohexanes] from 1-Cyano- and 1-Carbamoyl-5-methyl-4,5-dihydro-3H-spiro[benzo-2-azepine-3,1′-cyclohexanes]

Substitution of the nitrile group by hydroxylamine and hydrazine has been effected in 1-cyanodihydrospiro[benzo-2-azepine-3,1′-cyclohexane]. From the 1-cyano and 1-hydrazino derivatives tetrahydrospiro{1,2,3- and 1,2,4-triazolo[5,1-a]benzoazepine-5,1′-cyclohexanes} have been obtained. It was established that 1-carbamoyldihydrospiro[benzo-2-azepine-3,1′-cyclohexanes] are converted under the conditions of the Hoffmann reaction into spiro{diaziridino[3,1-a]benzo-2-azepine-3,1′-cyclohexane{, and is reduced by sodium borohydride to the tetrahydro derivative.

Amination of 4-Azafluorene under Chichibabin Reaction Conditions. Some Chemical Transformations of 1-Amino-4-azafluorene

Abstract4-Azafluorene is aminated by sodium amide in dimethylaniline at C(1). The oxidation of 1-amino-4-azafluorene was studied along with the condensation of this compound with acetic anhydride and its diazotization.

Synthesis and molecular structure of 4-nitro-9-phenyl-1H-and 9-hydroxy-3-oxo-9-phenyl-2,3-dihydro-9H-indeno-[2,1-c]pyridines and 3,7-diphenyl-3a, 4,5,6-tetrahydroindeno[2,1-c]isoxazolo[5,4-d]pyridine

The 4-nitro derivatives and an oxidation by-product, 9-hydroxy-2-methyl-3-oxo-9-phenyl-2,3-dihydro-9H-indeno[2,1-c]pyridine were obtained by the nitration of N-alkyl-9-phenyl-2,3-dihydro-1H-indeno-[2,1-c]pyridines with sodium nitrite in acetic acid. Their molecular structures were studied by X-ray structural analysis. The product of [2+3] cycloaddition, 5-methyl-3,7-diphenyl-3a, 4,5,6-tetrahydroindeno[2,1-c]isoxazolo[5,4-d]pyridine, was obtained by the interaction of 2-chloro-1-hydroxy-2-phenylazomethine with 2-methyl-9-phenyl-2,3-dihydro-1H-indeno[2,1-c]pyridine.

7-Dialkylaminomethyl-2,4,5-trimetyl-and 2,4,5-trimethyl-7-phenylminomethyl-1,2,3,4-tetrahydropyrrolo[1,2-c]pyrimidines

The Mannich aminoalkylation of 2,4,5-trimethyl-1,2,3,4-tetrahydropyrrolo[1,2-c]pyrimidine and condensation of its 7-formyl derivative with aniline have been studied. 7-Morpholinomethyl- and 7-(N-methylpiperazinylmethyl)-substituted derivatives have been isolated. 7-Dimenthylaminomethyl- and 7-phenyliminomethyl-substituted derivatives of tetrahydropyrrolo[1,2-c]pyrimidines are easiliy cleaved in the process of chromatographic isolation.

Reactions of 4,5-Dihydro-5-methyl-3H-spiro[benz-2-azepine-3-cyclohexane] N-Oxide with Some Nucleophilic Reagents

Abstract4,5-Dihydro-5-methyl-3H-spiro[benz-2-azepine-3-cyclohexane] N-oxide reacted with cyanide ion and isopropyl magnesium bromide to give the corresponding 1-cyano- and 1-isopropyl-4,5-dihydro-5-methyl-3H-spiro[benz-2-azepine-3-cyclohexane], but reaction with phenyl magnesium bromide, benzyl magnesium chloride, and nitromethane gave cyclic hydroxylamines: 1-substituted N-hydroxy-1,2,4,5-tetrahydro-5-methyl-3H-spiro[benz-2-azepine-3-cyclohexanes] which were oxidized to the corresponding nitrones.