Functionalized sulfur-containing compounds. 13. Synthesis of substituted 3-amino-2-(organylsulfinyl)-and-(organylsulfonyl)thieno[2,3-b]pyridines |
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Authors: | V. E. Kalugin A. M. Shestopalov V. P. Litvinov |
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Affiliation: | (1) N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation |
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Abstract: | A method for the synthesis of substituted 3-amino-2-(organylsulfinyl)thieno[2,3-b]pyridines by the Thorpe—Ziegler intramolecular cyclization of substituted 3-cyano-2-[(organyl-sulfinyl)methylthio]pyridines was proposed. 3-Amino-2-(organylsulfonyl)thieno[2,3-b]pyridines were obtained by reactions of substituted 3-cyanopyridine-2-thiones with chloromethyl organyl sulfones. The reaction intermediates 3-cyano-2-[(organylsulfonyl)methylthio]pyridines were transformed into 3-amino-2-(organylsulfonyl)thieno[2,3-b]pyridines. Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 510–515, March, 2006. |
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Keywords: | intramolecular cyclization the Thorpe— Ziegler reaction 3-cyanopyridine-2-thiones chloromethyl organyl sulfides chloromethyl organyl sulfones 3-cyano-2-[(organyl-sulfinyl)methylthio]pyridines 3-amino-2-(organylsulfinyl)thieno[2,3-b]pyridines 3-amino-2-(organylsulfonyl)thieno[2,3-b]pyridines |
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