Synthesis of substituted thienothiazoles
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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.
KeywordsPotassium Hydrolysis Hydrate Hydrochloride Disulfide
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- 1.P. I. Abramenko and V. G. Zhiryakov, Khim. Geterotsikl. Soedin., No. 12, 1624 (1970).Google Scholar
- 2.P. I. Abramenko, V. G. Zhiryakov, and T. K. Ponomareva, Sbornik Nauchn. Trudov Gosniikhimfotoproetka, Moskva, No. 13, 1–6 (1973).Google Scholar
- 3.N. I. Astrakhantseva, V. G. Zhiryakov, and P. I. Abramenko, Khim. Geterotsikl. Soedin., No. 12, 1607 (1975).Google Scholar
- 4.H. Larivé, P. Collett, and R. Dennilauler, Bull. Soc. Chim. Fr., No. 3, 1443 (1956).Google Scholar
- 5.F. M. Hamer, The Cyanine Dyes and Related Compounds, New York-London (1964), p. 58.Google Scholar
- 6.N. A. Damir and N. N. Sveshnikov, Zh. Vses. Khim. Ova, 10, 592 (1965).Google Scholar
- 7.K. Gewald, E. Schinke, and H. Bittecher, Ber., 99, 94 (1966).Google Scholar
- 8.K. Gewald, M. Hentschel, and R. Heikel, J. Prakt. Chem., 315, 539 (1973).Google Scholar