Synthesis of Spiranes by Cyclocondensation of 2-Phenacylbenzothiazole with Hydrazines and o-Hydroxybenzaldehydes

2-Phenacylbenzothiazole reacts with hydrazines and o-hydroxybenzaldehydes to give hydrazones and chalcones. These compounds tend to isomerize to benzothiazole-2-spiro-3'-pyrazoles and benzo[b]pyran-2-spiro-2'-benzothiazoles, respectively.     

Mass spectrometric study of mixed fluorinated rare earth element β-diketonates with triphenylphosphine oxide

A series of new adducts of fluorinated REE -diketonates with triphenylphosphine oxide was synthesized. The paths of their fragmentation under electron impact were investigated. It was shown that in contrast to the complex with 1,1,1,2,2,3,3-heptafluoro-7,7-dimethyloctane-4,6-dione, the complexes of europium with 1-trifluoromethoxy-1,1-difluoro-5,5-dimethylhexane-2,4-dione and 1, 1,1-trifluoro-5,5-dimethylhexane-2,4-dione form dimeric associates in the gaseous phase. The reasons for this difference in the behavior of the complexes and the possible structure of one of the dimers are discussed.Translated from Teoreticheskaya i Eksperimental'naya Khimiya, Vol. 26, No. 2, March–April, 1990.     

Synthesis of heterocyclic compounds on the basis of carboxylic acid arylamides

The exchange and cyclization of phenyliminooxalyl chloride with ammonium thiocyanate, sodium azide, aniline, amidoximes, and diphenylthiourea, and with 2-aminopyridine, 2-aminobenzothiazole, and 2-amino- and 2-mercaptobenzimidazole were studied. The cyclization products are derivatives of thiazolidine, imidazo[1,2-a]pyridine, imidazo[2,1-b]benzothiazole, imidazo[1,2-a]benzimidazole, and thiazolo[3,2-a]benzimidazole. A trimer of 1-phenyltetrazole-5-carboxylic acid was obtained when an attempt was made to convert its azide to the corresponding isocyanate.See [1] for communication II.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 471–474, April, 1971.     

6-Arylamino-3-methyl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazines: Novel N-Arylamidine Structures

We propose a method for obtaining derivatives of 7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine by alkylation of 4-amino-5-methyl-4H-1,2,4-triazole-3-thiol by substituted -chloroacetanilides, followed by cyclization of the intermediate by phosphorus oxychloride.     

Synthesis and Heterocyclization of 3-Arylaminothiocrotonanilides

Reactions of acetylthioacetanilide with arylamines in acetic acid in the presence of sodium acetate give 3-arylaminothiocrotonanilides in good yields. When treated with -bromoacetophenone in acetone, these products are converted to substituted 4-hydroxy-²-thiazolinium bromides, one of which was dehydrated to obtain the corresponding thiazolium bromide. The structure of the heterocyclization products was confirmed by single crystal X-ray diffraction and NMR study of 2-acetonylidene-3,4-diphenyl-2,3-dihydrothiazole formed by dehydration of the corresponding ²-thiazolinium salt with simultaneous hydrolysis.     

Use of Tetramethylthiuram Disulfide in Synthesis of Nitrogen-containing Heterocyclic Compounds

We have developed a method for synthesis of aryl isothiocyanates by means of thiocarbamoylation of aromatic amines by tetramethylthiuram disulfide followed by degradation of the intermediate N₍₁₎-aryl-N,N-dimethylthiourea by concentrated HCl. We have shown that thiocarbamoylation of 4-amino-5-ethyl-4H-1,2,4-triazole-3-thiol occurs at the 2 position of the triazole ring, while thiocarbamoylation of 4-amino-3-methyl-6-phenyl-4,5-dihydro-1,2,4-triazin-5-one leads to the dihetaryl-substituted thiourea. We consider the possibility of using N₍₁₎-aryl-N,N-dimethylthioureas as analogs of isothiocyanates in reactions with N-nucleophiles.__________Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 775–780, May, 2005.     

Synthesis and Transformations of 3-Ethoxycarbonyl-2-(N-R-thioureido)thiophenes

3-Ethoxycarbonyl-2-(N-R-thioureido)-4,5,6,7-tetrahydrobenzo[b]thiophenes were obtained by the reaction of 2-amino-3-ethoxycarbonyl-4,5,6,7-tetrahydrobenzo[b]thiophene with isothiocyanates and of 3-ethoxycarbonyl-2-isothiocyanato-4,5,6,7-tetrahydrobenzo[b]thiophene with primary and secondary amines. The cyclization paths of the products leading to derivatives of thieno[2,3-d]pyrimidine and thieno[2,3-d]-1,3-thiazine were studied. The corresponding S-substituted derivatives were obtained by the alkylation of 3-R-2-thioxo-3,4,5,6,7,8-hexahydrobenzo[b]thieno[2,3-d]pyrimidin-4-ones.     

Synthesis of 3-(Arylhydrazono)-5,5-di(hydroxymethyl)-2-oxomorpholines

Esters of (arylhydrazono)chloroacetic acid reacted with tris(hydroxymethyl)aminomethane in the presence of trimethylamine under mild conditions to give 3-(arylhydrazonoyl)-5,5-di(hydroxymethyl)-2-oxomorpholines.     

Study of Cryostructuring of Polymer Systems: 22. Composite Poly(vinyl alcohol) Cryogels Filled with Dispersed Particles of Various Degrees of Hydrophilicity/Hydrophobicity

Composite poly(vinyl alcohol) cryogels formed by the freezing–thawing of aqueous concentrated polymer solutions containing suspended filler were prepared and studied. The particles of unmodified silica gels were used as solid hydrophilic fillers and silica gels with grafted C2, C8, and C18 alkyl groups, as hydrophobic fillers. The granules of cross-linked dextran gel (Sephadex) swollen in water were used as soft hydrophilic fillers and lipophilic Sephadexes modified with propylene oxide groups, as soft hydrophobic fillers. It was shown that the microstructure and mechanical properties of such composites are affected by the presence of hydrophobic dispersed phase, namely, as the hydrophobicity of dispersed particles rises, the rigidity of composites increases with filler concentration at progressively lesser extent.     

Aminolysis of 2-Aryl-5-R-5,6-dihydro-7H-[1,2,4]triazolo[5,1-<Emphasis Type="Italic">b</Emphasis>]1,3]thiazin-7-ones

We have established that the products of aminolysis of 2-aryl-5-R-5,6-dihydro-7H-[1,2,4]triazolo-[5,1-b][1,3]thiazin-7-ones in boiling ethanol are 3-R-3-(5-aryl-4H-1,2,4-triazol-3-ylsulfanyl)-propanamides, and at 180°C–210°C (depending on the structure of the substituent R): 3-phenyl-4,5-dihydro-1H-1,2,4-triazoline-5-thione and 3-arylacrylamides or 3-(3-aryl-5-thioxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)propanamides. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1587–1592, October, 2005.