Researches on synthetic dyes

Reaction of phenyl-ß-naphthylamines with formaldehyde and acetone in the presence of HCl and nitrobenzene in butanol solution leads to cyclization involving the naphthalene and phenyl rings, and formation of N-aryllepidine salts. 15 lepidine and 5, 6-benzoepidine salts are synthesized and characterized by their UV absorption spectra, as well as by their picrates.For Part LIII see [3].     

Topochemical investigations of peptide systems

The basic principles of the topochemical approach to the investigation of the structure-function relation in peptide systems are formulated. This approach makes use of the new possibility of transforming natural peptides, consisting in the modification of the molecule as a whole and utilization of the resultant analogs to elucidate the boundaries of the stereoelectronic complementarity of the biologically active peptide to the corresponding receptor. In particular, on the example of depsipeptide antibiotics and their topochemical analogs the fruitfulness of using such compounds as tools in elucidating the physicochemical basis of functioning of biological membranes is shown. The topochemical principle has also been applied in preparing specific competitive inhibitors of proteolytic enzymes, whose study may shed light on the nature of the forces binding the substrate to the contact site of the corresponding enzyme.     

Studies on organophosphorus compounds—V: Pyridines from secondary car☐amides and HMPA

A new pyridine synthesis has been found by refluxing certain simple secondary car☐amides in HMPA. Thus 2,6-dimethylpyridine, 2-ethyl-6-methylpyridine, 2,3,6-trimethylpyridine, 2-ethyl-3,6-dimethylpyridine, 2-benzyl-6-methyl-3-phenylpyridine, 2-ethyl-3-methyl-5,6,7,8-tetrahydroquinoline and 2-t-butyl-6-methylpyridine were prepared in 15–40% yield.     

Structure,tautomerism, and transformations of β-(3-nitro-2-pyridyl)- and β-(3-nitro-4-pyridyl)pyruvic acid esters

It was shown by means of IR, UV, and PMR spectra that -(3-nitro-2-pyridyl)pyruvic acid esters are practically completely enolized in the crystal state and in solution; ethyl -(3-nitro-4-pyridyl)pyruvate has an enol structure in the crystalline state and in pyridine solution but exists as a mixture of keto and enol forms in low-polarity solvents.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 389–393, March, 1974.     

A new synthesis of ampicillin and related investigations

Quaternization of (S)-α-bromophenylacetic acid amide (8) with hexamethylentetramine (hexamine) preceded with ca. 80% inversion of configuration. Accordingly, starting from the trimethylsilylester of N-(S)-(α-bromo-α-phenylacetyl)-6-aminopenicillanic acid (4) quaternization with hexamine and subsequent hydrolysis afforded N-(R)-α-phenylglycyl-6-aminopenicillanic acid (1, ampicillin). Some other model reactions have been investigated.     

Synthesis,alkylation, and molecular and crystal structure ofN-methylmorpholinium 6-amino-3,5-dicyano-1,4-dihydropyridine-4-spirocyclohexane-2-thiolate

The reaction of cyano(cyclohexylidene)thioacetamide with cyanothioacetamide or malononitrile andN-methylmorpholine yieldsN-methylmorpholinium 6-amino-3,5-dicyano-1,4-dihydropyridine-4-spirocyclohexane-2-thiolate. Its structure was established based on the results of alkylation and X-ray structural analysis.Deceased.Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 2535–2540, October, 1996.