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Cyanine dyes with an isoindolenine ring in the chromophore

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

2-[3-(3-Methyl-2-benzothiazolinylidenyl)-1-methylisoindolinylidenyl]methyl-3-methylbenzothiazolium perchlorate was obtained by the condensation of 2-methylbenzothiazole methylmethosulfate with 1,1,3-trichloroisoindolenine. Similar dyes of the pyridine and quinoline series were also synthesized. The absorption bands of the cyanine dyes with an isoindolenine ring in the chromophore are shifted by 30 nm to the shortwave region in comparison with the corresponding dicarbocyanines. Acids protonate the dyes at the isoindolenine ring to form compounds with two conjugated chromophores. Condensation of 1,1,3-trichloroisoindolenine with N-substituted rhodanines yields 3-substituted 5-[3-(3-methyl-4-hydroxythiazoline-2,5-thionyl)-1-isoindolinylidene]rhodanines. Alkylation and hydrolysis of the N-methyl substituted dye yields 5-[3-(3-methyl-4-hydroxy-5-thiazolin-5-onyl)isoindolinylidene-1]-3-methylthiazolidine-2, 4-dione.

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Authors and Affiliations

  1. Institute of Organic Chemistry, Academy of Sciences of the UkrainianSSR, Kiev

    A. Ya. Il'chenko & I. D. Radchenko

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  1. A. Ya. Il'chenko
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  2. I. D. Radchenko
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 454–458, April, 1971.

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Il'chenko, A.Y., Radchenko, I.D. Cyanine dyes with an isoindolenine ring in the chromophore. Chem Heterocycl Compd 7, 423–427 (1971). https://doi.org/10.1007/BF00471476

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  • DOI: https://doi.org/10.1007/BF00471476

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