Polymethylene dyes derived from heterocyclic bases containing condensed thiophene rings

Some new polymethine dyes of the cyanine and merocyanine series which are derivatives of 5- and 6- thienopyridines are synthesized. Replacement of a vinyl group at a sulfur atom in the condensed benzene ring of quinoline in dyes which are derivatives of this base, always leads to a bathochromic shift of the absorption maximum of the corresponding dyes.     

Synthesis and properties of 8-phenylindolo-3,3′-trimethinecyanines

The condensation of 1-methyl-2-aryl-3-(2-benzoylvinyl)indoles with substituted indoles in acetic anhydride in the presence of a mineral acid afforded 8-phenylindolo-3,3-trimethinecyanines. Their spectral, polarographic, and photographic properties were studied.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 499–501, April, 1992.     

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.     

Methyl-substituted heterocyclic bases containing condensed selenonaphthene rings

The synthesis of 2-methylselenonaphtheno[2,3-d]thiazole and 2-methylselenonaphtheno[2,3-d]-oxazole is described.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 37–38, January, 1971.     

Structure of 2,4-diamino-6-(2,4-diphenyl-1-cyano-1,3-butadien-1-yl)-5-cyano-nicotinonitrile

An x-ray diffraction structural analysis was carried out to determine the structure of the 12 solvate of 2,4-diamino-6-(2,4-diphenyl-1-cyano-1,3-butadien-1-yl)-5-cyano-nicotinonitrile with acetonitrile (I) using Mo radiation to R=0.043. The unit cell parameters of the monoclinic crystals of I are as follows: a=11.019, b=23.541, c=9.861 Å, =105.45°, d _calc =1.27, Z=4, space group P2₁/c. The nonplanar, sterically strained molecule has trans configuration with E arrangement of the substituents in the butadiene fragment. The molecular packing in the crystal solvate is determined by the hydrogen bonding between the amino and cyano groups and coulombic interactions due to the polar nature of the acetonitrile molecules. The effect of the substituents on the pyridine ring geometry, analogous to that reported for benzene derivatives, is discussed.Research Institute for Organic Intermediates and Dyes and A. N. Nesmeyanov Institute of Heteroorganic Compounds, Academy of Sciences of the USSR. Translated from Zhurnal Strukturnoi Khimii, Vol. 30, No. 5, pp. 114–122, September–October, 1989.     

Synthesis of substituted thienothiazoles

The action of sulfur monochloride on 2-amino-3-carboxy-5-phenylthiophene or 2-amino5-phenylthiophene hydrochloride gave 5-phenylthieno[2,3-d]-2-thioniathiazole chloride, which is converted to the corresponding hydrate on treatment with water. Heating of the thionium salt or its hydrate with carbon disulfide in an aqueous alcohol solution of aklaki gave 2-mercapto-5-phenylthieno[2,3-d]thiazole, which under the influence of dialkyl sulfates or on oxidation with potassium permanganate in alkaline media is converted, respectively, to S-alkyl derivatives or a 5-phenylthieno[2,3-d]thiazole-2-sulfonic acid salt. 2-Sulfo-3-alkylthieno[2,3-d]thiazolium betaines are obtained by heating the latter with alkylating agents. 2-Hydroxy-thieno[2,3-d]thiazoles were synthesized by hydrolysis of thienothiazole-2-sulfonic acids.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 477–480, April, 1979.     

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.     

Synthesis of 7-methyl- and 9-methylthieno[3, 2-f]quinoline

New heterocyclic bases with a condensed heterocyclic ring in the molecule are synthesized. They are 7-methylthieno[3, 2-f ]quinoline and 9-methylthieno[3, 2-f]quinoline.     

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.     

Polymethine dyes which are derivatives of heterocyclic bases containing condensed thiophene rings

Some new polymethine dyes of the cyanine and merocyanine series, containing thieno[2, 3-b]thieno[2, 3-b]pyridine-4 and thieno[3, 2-b]-thieno[2, 3-b]-pyridine-8 groups are synthesized. Replacement of the vinylene group by a sulfur atom in the condensed benzene rings of the 5, 6-benzoquinoline-4 group in dyes which are derivatives of this base, results in a marked hypsochromic shift of the absorption maximum of the corresponding dyes.For Part IV see [8].