Investigations in the field of perinone compounds

A simple method for preparing perinones from peri-dinitro compounds has been obtained. It has been shown that the reaction takes place via the formation of naphthalene-1, 8-diamine and 2-(2-carboxyphenyl)-perimidine.     

Investigation of perinone compounds

The electronic nature of the substituent in naphthalic anhydride has a substantial effect on the isomeric composition of the naphthaloperinones formed in reactions with 1,8-naphthylenediamine. An electron-accepting substituent in the 4 position of naphthalic anhydride promotes predominant retention of the carbonyl group in the 1 position, while an electrondonating substituent promotes retention of the carbonyl group in the 8 position of the naphthalene ring. 10-Amino- and 11-amino-14H-benzo[4,5]isoquinolino[2,1-a]perimidin-14-ones were synthesized.For Communication II see [1].Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1420–1422, October, 1970.     

Research on perinone compounds

11-Substituted 14H-benz[4,5]isoquinolino[2,1-a]perimidin-14-ones were synthesized, and their spectra were studied. In contrast to electron-acceptor substituents, electron-donor substituents have little effect on the shift of the absorption maxima. In the reactions of 1,8-naphthalenediamine with various 4-substituted naphthalic anhydrides, electron-donor substituents have little effect on the shift of the absorption maxima. In the reactions of 1,8-naphthalenediamine with various 4-substituted naphthalic anhydrides, electron-donor substituents lead primarily to 10-substituted naphthaloperinones, whereas electron-acceptor substituents lead primarily to 11-substituted naphthaloperinones. An assumption regarding the mechanism of the formation of 10- and 11-substituted naphthaloperinones is expressed.See [1] for communication IV.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1649–1654, December, 1974.     

Research on perinone compounds

10-Substituted 14H-benz[4,5]isoquinolino[2,1-a]perimidin-14-ones were synthesized, and their spectra were studied. In contrast to electron-acceptor substituents, electron-donor substituents have little effect on the shift of the absorption maxima.See [1] for communication III.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1388–1390, October, 1973.     

Investigations in the field of 1-aza bicyclic compounds

As the result of a study of the condensation of acrylonitrile and 1,2-dihydropyrrolizines in the presence of AlCl₃, 5-cyanoethyl-1,2-dihydropyrrolizines have been synthesized. Some of the properties of the compounds obtained have been studied and their IR spectra have been recorded.For part VI, see [1].     

Investigations in the imidazole field

It has been established that various inorganic and organic bases can be used for the cyclization of 1,2-dialkyl-3-(-oxoalkyl[aralkyl])benzimidazolium halides into derivatives of pyrrolo[1,2-a]benzimidazole. The action of strong bases on quaternary benzimidazolium salts gives O-betaines—intermediates in the closure of the pyrrole ring.For part XL, see [1].     

Investigations in the field of lipids

Summary A method for the separate quantitative determination of the furocoumarins ofFicus carica has been developed.Khimiya Prirodnykh Soedinenii, Vol. 3, No. 5, pp. 295–298, 1967     

Investigations in the field of tetracyclines

Summary The synthesis of 4-N-desdimethyl- (IIa) and 4-N-desmethyl-12a-deoxy-5a,6-anhydrotetracycline (IIb) has been effected.For preliminary communications, see [1].M. M. Shemyakin Institute of the Chemistry of Natural Compounds of the Academy of Sciences of the USSR. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 357–363, May–June, 1971. Original article submitted Feburary 26, 1971.     

Investigations in the field of lipids

Summary A number of derivatives of androstano [3, 2-b] pyrylium and androst-13-eno-[3, 2-b] pyrylium derivatives forming a new class of heterocyclic steroids has been obtained.Khimiya Prirodnykh Soedinenii, Vol. 1, No. 5, pp. 318–321, 1965     

Investigations in the field of lipids

Summary 1. The synthesis of the following neutral plasmalogens has been effected: -O-(octadec-1-enyl)-, distearoylglycerol, -O-(octadec-1-enyl)-, -dipalmitoylglycerol, -O-(hexadec-1-enyl)-, -distearoylglycerol, and -O-(pentadec-1-enyl)-, -dipalmitoylglycerol.2. During the synthesis, the following compounds were isolated and characterized by their physicochemical constants: the -octadec-1-enyl ether of glycerol, -(2-hydroxyoctadecyl) , -isopropylideneglyceryl ether, the tosylate of -(2-hydroxyoctadecyl) , -isopropylideneglyceryl ether, and -O-(2-tosyloxyoctadecyl) glycerol.3. The IR spectra of the -octadec-1-enyl ether of glycerol and the neutral plasmalogens have been studied.Khimiya Prirodnykh Soedinenii, Vol. 2, No. 6, pp. 367–371, 1966     

Investigations in the field of anthrapyridone

6-Bromo-N-methylpyridone reacts with phosphorus pentachloride at 180° C to form, 2, 6-dichloroanthrapyridine. The latter reacts with amines at moderate temperatures forming 6-amino-2-chloro derivatives of anthrapyridine and at high temperatures forming 2, 6-diamino-substituted anthrapyridines.For part III, see [1].     

Investigations in the field of polymerocyanines

A series of N-acyl-1, 2, 3, 4-tetrahydro-4-alkyl(aryl)iminobenzo[g]quinolines has been obtained by the condensation of N-acyl-1, 2, 3, 4-tetrahydro-4-oxobenzo[g]quinolines with primary amines.For part IV, see [1].     

Investigations in the field of polymerocyanines

Dimerocyanines containing rhodanine residues with an alkyl or a substituted alkyl group on the nitrogen atom have been synthesized. The influence of these substituents on the color and photo properties of these dimerocyanines and their solubility in ethanol has been studied.For part I, see [2].