Synthesis and transformations of 3-(1H-pyrrol-1-yl)thieno[2,3-b]pyridines |
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Authors: | E. A. Kaigorodova A. A. Osipova L. D. Konyushkin G. D. Krapivin |
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Affiliation: | (1) Kuban State Technological University, 2 ul. Moskovskaya, 350072 Krasnodar, Russian Federation;(2) N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation |
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Abstract: | Reactions of 2,5-dimethoxytetrahydrofuran with 3-aminothieno[2,3-b]pyridines afford a number of substituted 3-(1H-pyrrol-1-yl)thieno[2,3-b]pyridines. The possibility of the reaction and the yield of the product are determined by the character of a substituent in position 2 of thieno[2,3-b]pyridine. The Curtius rearrangement of 2-acylazido-3(1H-pyrrol-1-yl)thieno[2,3-b]pyridines yields 4,5-dihydropyrido[3",2":4,5]thieno[2,3-e]pyrrolo[1,2-a]pyrazin-4-ones. The molecular and crystal structures of ethyl 4-methoxymethyl-6-methyl-3-(1H-pyrrol-1-yl)thieno[2,3-b]pyridine-2-carboxylate were determined by X-ray diffraction analysis. |
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Keywords: | 3-aminothieno[2,3-b]pyridines 2,5-dimethoxytetrahydrofuran 3-(1H-pyrrol-1-yl)thieno[2,3-b]pyridines 4,5-dihydropyrido[3" ,2" :4,5]thieno[2,3-e]pyrrolo[1,2-a]pyrazin-4-ones IR spectroscopy UV spectroscopy 1H NMR spectroscopy 13C NMR spectroscopy X-ray diffraction analysis |
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