V. G. Voronin

Reaction of l-(p-nitrophenyl)-2-acetylamino-l,3-propanediol with sodium hypochlorite

At one of the conclusive stages in the synthesis of the levomycetin antibiotic, a racemic mixture of RIR 2and StS2-1-(p-nitrophenyl)-2-amino-l,3-propanediols is formed, but only the R:R2-isomer is used for the preparation of the biologically active compound. Equal amounts of the S*S2-isomer (dextramine, Ia) thus formed are not utilized and comprise a very expensive and high volume waste in the production of levomycetin.

Reaction of phenylhydrazides of N-acyl-?-phenyl-?-alanine with phosphorus oxychloride

The reaction of N′-methyl-N′-phenylhydrazides of N-acyl-β-phenyl-β-alanine with phosphorus oxychloride is accompanied by cleavage of the C-N bond in the intermediately formed 2-aminoindole derivative and, after splitting out of an amide fragment, leads to 1-methyl-3-benzylidene-2-iminoindoline and nitriles. Pyrimido [4,5-b] indoles — products of cyclization of the corresponding intermediate 2-aminoindole derivatives — were isolated from the reaction mixtures in low yields. The structure of 1-methyl-3-benzylidene-2-iminoindoline was proved by alternative synthesis.

Synthesis of 2-amino-3-(?-aminoalkyl)indoles

Abstract2-Amino-3-(ω-phthalimidoalkyl)indoles have been obtained by the rearrangement of ω-phthalimido acid β-phenylhydrazides under the action of POCl3. The possibility has been studied of eliminating the phthalyl protective group from these compounds and a convenient method has been developed for obtaining 2-amino-3-(ω-aminoalkyl)indole dihydrochlorides. The behavior of the 2-amino-3-(ω-phthalimidoalkyl) indoles in alkylation reactions has been investigated.

meta-Substituted arylhydrazides in the Kost reaction

Kost cyclization of meta-substituted arylhydrazides results primarily in the formation of mixtures of 4- and 6-substituted 2-aminoindoles.

SYNTHESIS AND BIOLOGICAL ACTIVITY OF 4-ARYL (AND ARALKYL)IMINOBARBITURIC ACIDS

A study of the chemical structure--antiinflammatory action relationship in a number of the examined compounds showed that a chlorine atom in the para position of the benzene ring and chlorine atoms in the 2,4-positions lead to a marked reduction in antiinflammatory activity. An even greater reduction in antiinflammatory activity results from the placement of the benzene rings nitro group in the meta position, whereas an iodine atom in the meta position leads to a marked increase in antiinflammatory activity. Increased activity is also observed when the nitro group is in positions 3, 4, 5 of the benzene ring, and when a methoxy group is in the ortho position.

Regioselectivity of the rearrangement of propionic acid N,N-diarylhydrazides under the conditions of the kost reaction

The transformation of propionic acid N,N-diarylhydrazides with electron-donor and electron-acceptor substituents in the aromatic rings under the conditions of the Kost reaction was studied. The ratios of the resulting isomeric N-aryl-2-aminoindoles were determined.

Synthesis of 10-phthalimidoalkyltetrahydropyrimido[1,2-a]-indoles

Abstract10-Phthalimidoalkyltetrahydropyrimido [1,2-a] indoles were obtained by rearrangement of cyclic hydrazides of N-phthalyl-ω-amino acids, viz., 1-phenyl-2-acyl-pyrazolidines, under the influence of phosphorus oxychloride.

Synthesis of 2- and 6-arylaminopyrimidinediones

Methods for the synthesis of 6-arylamino-5,5-diethyl-3H,5H-pyrimidine-2,4-diones from the corresponding 6-thioxo and 6-amino derivatives were developed. The isomeric 2-arylamino-5,5-diethyl-1H,5H-pyrimidine-4,6-diones were obtained by the reaction of 2-mercapto- and 2-methylthio-1H,5H-pyrimidine-4,6-diones with substituted anilines. The ionization constants of the compounds obtained were determined.

Synthesis of 1-aryl-3-(3-pyrrolyl)-5-oxopyrazoles

Abstract1-Aryl-3-(2,4-dimethyl-5-ethoxycarbonyl-3-pyrrolyl)-5-oxopyrazoles were obtained by condensation of ethyl β-(2,4-dimethyl-5-ethoxycarbonyl-3-pyrrolyl)-β-ketopropionate with arylhydrazines. Electron-donor substituants in the aromatic ring of the arylhydrazines accelerate the cyclization of the intermediate hydrazones, whereas electron-acceptor substituents hinder cyclization.

Synthesis and reactions of 2-amino-3-(ω-chloroaklyl)indoles

The reaction of N-methyl-N-phenyl-N′-(ω-chloro)acylhydrazines with POC13 yields derivatives of 2-amino-3-(ω)-chloroalkyl) indoles. Hydrazides of β-chloropropionic acid were found to exist as the cyclic quaternary 3-oxopyrazolidinium salt. Several reactions involving the nucleophilic substitution of the chlorine atom in N-acylated derivatives of 2-aminoindole were studied.