Synthesis of 6-aryl- and 5-aroylcomanic acids from 5-aroyl-2-carbethoxy-4-pyrones via a deformylative rearrangement and ring-opening/ring-closure sequence |
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Authors: | Dmitrii L. Obydennov,Gerd-Volker Rö schenthaler,Vyacheslav Ya. Sosnovskikh |
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Affiliation: | 1. Department of Chemistry, Ural Federal University, prosp. Lenina 51, 620000 Ekaterinburg, Russia;2. School of Engineering and Science, Jacobs University Bremen, Campus Ring 1, 28759 Bremen, Germany |
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Abstract: | The reaction of 1-aryl-2-(dimethylaminomethylene)butane-1,3-diones with diethyl oxalate in the presence of sodium hydride in THF gave ethyl 5-aroyl-4-oxo-4H-pyran-2-carboxylates, from which 4-oxo-6-aryl-4H-pyran-2-carboxylic acids (6-arylcomanic acids) were obtained in high yields via acid-catalyzed deformylative rearrangement. 5-Aroyl-4-oxo-4H-pyran-2-carboxylic acids (5-aroylcomanic acids) were prepared via а ring-opening/ring-closure sequence by the reaction of 5-aroyl-2-carbethoxy-4-pyrones with piperidine and subsequent basic hydrolysis and acidification. |
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Keywords: | Claisen condensation 2-(Aminomethylene)butane-1,3-diones 5-Aroyl-2-carbethoxy-4-pyrones Rearrangement 6-Arylcomanic acids 5-Aroylcomanic acids |
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