Synthesis of 2-phenylthieno[3,2-d]oxazole and 2-phenylthieno[3,2-d]thiazole

2-Phenylthieno[3,2-d]oxazole and 2-phenylthieno[3,2-d]thiazole were obtained by cyclization of the corresponding 2-phenyloxazole and 2-phenylthiazole derivatives. Their spectra and chemical properties were studied, and the pK_a values of carboxylic acids with other two-ring systems with a condensed thiophene ring were also compared.See [1] for our preceding communications.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 474–476, April, 1979.     

Polymethine dyes — Indolo[3,2-d]thiazole derivatives

New polymethine dyes with an indolo[3,2-d]thiazole residue are described, and their spectral properties are discussed. Replacement of the vinylene group in the naphtho[1,2-d]thiazole residue by an NH group leads to a considerably greater bathochromic shift of the absorption maximum of carbo- and merocyanines as compared with replacement by a sulfur atom. The basicity of the indolo[3,2-d]thiazole residue is higher than the basicity of the naphtho[1,2-d]-thiazole and thionaphtheno[3,2-d]thiazole residues.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1606–1610, December, 1972.     

Synthesis of 2-methylthie no [3,2-b]thieno-[2,3-d]thiazole

A new heterocyclic base — 2-methylthieno[3,2-b]thieno[2,3-d]thiazole — was synthesized by heating 2-acetamido-3-hydroxythieno[3,2-b]thiophene with phosphorus pentasulfide.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1039–1041, August, 1976.     

Selenium heterocycles. XXVIII . Synthesis of pyrrolo[3,2-d]selenazole and pyrrolo[3,2-d|thiazole. Two novel heterocycles

Starting from the readily available 2-substituted-4-formylselenazoles and 2-substituted-4-formylthiazoles, a series of substituted-pyrrolo[3,2-d]selenazoles and substituted-pyrrolo[3,2-d|-thiazoles were prepared respectively.     

New Synthesis of Pyrido[2,3-d] and [3,2-d]Oxazines

N-Hydroxyquinolinimide 1 reacts with each of aromatic amines, hydrazine hydrate and aromatic hydrocarbons to give arylcarbamoyl pyridines 2, pyrrolopyridines 3, pyridopyridazines 4 and pyridooxazinones 5 and 6. The heterocycles 5 and 6 can be transformed to the condensed systems, triazolopyridopyridazines 14 and 15 through series of reactions.     

Selenonaphtheno[2,3-d]thiazole derivatives as polymethine dyes

New polymethine dyes — selenonaphtheno[2,3-d]thiazole derivatives — were synthesized. It is shown that all of the synthesized dyes which have a selenonaphtheno[2,3-d]thiazole residue are more deeply colored than the corresponding 6,7-benzobenzothiazole and thionaphtheno[2,3-d] thiazole derivatives.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 459–461, April, 1971.     

Synthesis of new pyrido[2,3-d]pyrimidine derivatives

The mutual condensation of 4-aminouracil or 2,4-diamino-6-hydroxypyrimidine with bisacetonitrile and aldehydes was used to synthesize 2,4-dioxo-5-R-7-methyl-6-cyano-1,2,3,4,5,8-hexahydropyrido[2,3-d]pyrimidine and 2-amino-4-oxo-5-R-7-methyl-6-cyano-3,4,5,8-tetrahydropyrido[2,3-d]pyrimidine derivatives, which were oxidized with chromic anhydride to the corresponding 2,4-dioxo-5-R-7-inethyl-6-eyano-1,2,3,4-tetrahydropyrido[2,3-d]pyrimidine and 2-amino-4-oxo-5-R-7-methyl-6-cyano-3,4-dihydro[2,3-d]pyrimidines. The IR and UV spectra of the synthesized compounds were recorded.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 422–425, March, 1972.     

Synthesis of substituted thieno[2,3-d]thiazoles and indolo[3,2-d]thiazoles

Alkylene-, halo-, and aryl-substituted 2-methylthieno[2,3-d]thiazoles were obtained by the action of phosphorus pentasulfide on the corresponding 2-acetylamino-3-bromo- or 2-acetylamino-3-hydroxythiophenes in an organic solvent with heating. 2-Oximes of halo- and methyl-substituted isatins were converted by reduction and acylation into 2-hydroxy-3-acetylaminoin-doles, from which 2-methylindolo[3,2-d]-thiazoles were obtained by the action of phosphorous pentasulfide with heating in xylene.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 410–417, March, 1987.     

Synthesis of 2-Carbamoylthieno[3,2-d]thiazoles

A preparation procedure was developed for previously unknown 2-carbamoylthieno[3,2-d]-thiazoles consisting in cyclization effected by K₃Fe(CN)₆ of monothiooxamides obtained from 2-methyl-4-aminothiophene, chloroacetamides, and sulfur in the presence of triethylamine.     

Selenium heterocycles XXVII . Synthesis of Thieno[2,3-d] thiazole and Selenolo[3,4-d]thiazole. Two novel heterocycles

Starting from the readily available aryl 2-substituted-4-methyl-5-thiazolyl ketones, a series of 2,6-disubstituted-thieno[3,4-d]thiazoles and 2,6-disubstituted-selenolo[3,4-d]thiazoles were prepared. The structures of these compounds were confirmed by analytical, spectroscopic methods and through the reaction with dimethyl acetylenedicarboxylate.     

Synthesis of a novel series of 3-substituted [1]benzothieno[3,2-d]pyrimidine derivatives

A series of 3-substituted [1]benzothieno[3,2-d]pyrimidine derivatives has been synthesized as possible antileukemic agents by condensation of methyl 3-(ethoxymethylene)amino-2-benzothiophene carboxylate (II) with a variety of amines to afford the corresponding 3-aryl and 3-alkyl [I]benzothieno[3,2-d]pyrimidin-4(3H)-ones, Ill and IV, respectively. In addition, Mannich reactions of [I]benzothieno[3,2-d]pyrimidin-4(3H)-one (VIII) with formaldehyde and secondary amines gave the expected derivatives, IX. 3-Amino[I]benzothieno[3,2-d]-pyrimidin-4(3H)-one (VI) reacted with substituted aromatic aldehydes in the presence of boron trifluoride to yield the corresponding imines VII.     

Synthesis of furo[3,2-c]pyridine and furo[2,3-d]pyrimidine derivatives from butyrolactone diethylacetal

The reaction of butyrolactone acetal with CH acids was used to synthesize 2-methylenetetrahydrofuran derivatives. The latter react with dimethylformimide acetal to give a dieneamine that is capable of undergoing cyclization to furo [3,2-c]pyrimidine derivatives. This two-ring system was also synthesized by the reaction of cyanacetamide with 3-dimethylaminomethylenebutyrolactone acetal. The indicated acetal can also react with amidine components to give furo [2,3-d]pyrimidine derivatives.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 68–71, January, 1982.     

Synthesis of 2-R-fluorantheno[2,3-d]- and 2-R-fluorantheno[3,2-d]oxazoles

2-R-Fluorantheno[2,3-d]- and 2-R-fluorantheno[3,2-d]oxazoles were synthesized, and their UV and IR spectra were studied. Ten new compounds are described.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 905–907, July, 1974.     

Polymethine dye derivatives of pyrazolo[4, 5-d]thiazole

Quino(2)monomethine-, carbo-, mero-, dimero-, and rhodacyanines, as well as styryl dyes containing 4-methyl-6-phenyl- and 4, 6-diphenlpyrazolo[4, 5-d]thiazoles groupings are prepared. Study of the colors of the synthesized dyes, showed that dyes containing a pyrazolo[4, 5-d]moiety to be considerably more deeply colored, than the corresponding benzothiazole derivatives.     

Synthesis of New Fused Thieno[3,2-d]pyrimidines Based on Thieno[3,2-d][1,3]oxazine Derivative

Russian Journal of General Chemistry - A method was developed for the synthesis of new fused amines, thieno[3,2-d]pyrimidine derivatives, starting from the corresponding chloride and various...     

Synthesis of 2-methylphenanthro[2, 1-d]thiazole

2-Methylphenanthro[2, 1-d]thiazole has been synthesized by the oxidative cyclization of 2-thioacetylaminophenanthrene.     

Synthesis of 2-methyl-5-phenylthieno[2,3-d]thiazole

The synthesis of a new heterocyclic base — 2-methyl-5-phenylthieno[2,3-d]thiazole — is described.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, 1624–1625, December, 1970.     

Mass spectra of imidazo[2,1-b]thiazole and thiazolo[3,2-f]xanthene derivatives

The general principles of the mass-spectrometric disintegration of imidazo [2,1-b]thiazole and thiazolo[3,2-f]xanthene derivatives were established, and the characteristic fragments were identified. Disintegration proceeding with cleavage of the bonds in the thiazole ring of the 2(3)-ring system is characteristic of all of the investigated compounds. The cleavage of the S-C bonds, which are the weakest in the investigated systems, proceeds especially readily. Intense peaks of ions due to stepwise disintegration of the pyrimidine ring are also observed in the spectra of thiazoloxanthenes.     

Synthesis of 2-mercapto-substituted thieno[2,3-d]thiazoles and ben zothieno[3,2-d] thiazoles

2-Mercaptothieno[2, 3-d]thiazoles were synthesized from bis(2-nitro-3-thienyl) disulfide by successive reduction of, initially, the disulfide bond and the nitro group in the presence of carbon disulfide without isolation of the intermediate 2-nitro-3-mercaptothiophene. 2-Mercaptobenzo-[b]thieno[3, 2-d]thiazole was synthesized by reaction of 3-aminobenzo[b]thiophene hydrochloride with sulfur monochloride and cleavage of the resulting benzo[b]thienothiazothionium chloride with sodium sulfide in the presence of carbon disulfide.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1355–1356, October, 1976.     

High molecular weight broad band-gap polymers based on indolo[3,2-b]carbazole and thiazolo[5,4-d]thiazole derivatives for solar cells

Two broad band-gap high molecular weight polymers, poly[(5,11-di(9’-heptadecanyl)-indolo[3,2-b]carbazole-alt-2,5-bis(3-n-octylthiophene-2-yl)-thiazolo[5,4-d]thiazole (PICzOTzTz) and poly[(5,11-di(9’-heptadecanyl)-indolo[3,2-b]carbazole-alt-2,5-bis(3-n-n-dodecylthiophene-2-yl)-thiazolo[5,4-d]thiazole]) (PICzDOTzTz), consisting of indolo[3,2-b]carbazole (ICz) and thiazolo[5,4-d]thiazole (TzTz) derivatives were synthesized by Suzuki polycondensation. Their physical, electrochemical and optical properties were characterized in details. The thermogravimetric analysis displayed high thermal stability, and 5% degradation temperatures of PICzOTzTz and PICzDOTzTz were 427 and 435°C, respectively. The optical band gaps of PICzOTzTz and PICzDOTzTz were 2.13 and 2.07 eV, respectively. The hole mobilities of PICzOTzTz and PICzDOTzTz were investigated by the space charge limited current (SCLC) method, which gave the mobility values of 7.21 × 10^–5 and 1.57 × 10^–4 cm²/(V s) for each polymer, respectively. Through the photo-voltaic characterization in polymer solar cells, they showed that the power conversion efficiencies of PICzOTzTz and PICzDOTzTz were 0.64 and 0.99%, respectively.