One-pot synthesis of 2-substituted thieno[3,2-b]indoles from 3-aminothiophene-2-carboxylates through in situ generated 3-aminothiophenes |
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| Institution: | 1. Postovsky Institute of Organic Synthesis, Ural Division, Russian Academy of Sciences, S. Kovalevskoy Str., 22, Ekaterinburg 620990, Russia;2. Ural Federal University named after the First President of Russia B. N. Yeltsin, Mira Str., 19, Ekaterinburg 620002, Russia;1. Department of Polymer Chemistry and Technology, Kaunas University of Technology, Radvilenu pl. 19, LT-50254 Kaunas, Lithuania;2. Department of Solid State Electronics, Vilnius University, Sauletekio al. 9-III, LT-10222 Vilnius, Lithuania;1. A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 664033 Irkutsk, Russian Federation;2. Laboratory of Quantum Chemistry, Irkutsk State University, 664003 Irkutsk, Russian Federation;3. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 119991 Moscow, Russian Federation;1. Department of Animal Science, University of Tehran, P.O. Box 4117, Pakdasht, Tehran, Iran;2. Nuclear Science & Technology Research Institute, P.O. Box 31485498, Karaj, Iran;1. Institute of Physics, Polish Academy of Sciences, Aleja Lotników 32/46, PL-02668 Warsaw, Poland;2. Medical University of Warsaw, ?wirki i Wigury 61, PL-02091 Warsaw, Poland |
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| Abstract: | A convenient protocol for one-pot synthesis of thieno3,2-b]indoles, bearing aromatic, thien-2-yl or styryl fragments at C-2 position, from easily accessible 5-substituted 3-aminothiophene-2-carboxylates using the Fischer indolization reaction, was developed during this study. Two main steps of this approach are the saponification of the starting 3-aminoesters with sodium hydroxide and next treatment of the crude 3-aminoacids sodium salts with arylhydrazines in glacial acetic acid solution. The latter step includes in situ decarboxylation of the freed 3-aminothiophene-2-caboxylic acids to the 3-aminothiophenes and their acid promoted reaction with arylhydrazines to initially form arylhydrazones of 5-substituted thiophene-3(2H)-ones, which smoothly cause indolization to afford the desired thieno3,2-b]indoles. |
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| Keywords: | 3-Aminothiophene Arylhydrazines The Fischer indole synthesis |
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