Please use this identifier to cite or link to this item:
http://repo.knmu.edu.ua/handle/123456789/19212
Title: | Two-stage one-pot interaction of acyclic β-ketoesters, DMFDMA and 2-cyanomethylbenzimidazole |
Authors: | Vodolazhenko, Mariya Mykhailenko, Anastasia Gorobets, Nikolay Desenko, Sergey |
Keywords: | β-ketoester 2-cyanomethylbenzimidazole one-pot heterocyclization DMFDMA microwave irradiation |
Issue Date: | 2017 |
Publisher: | ХНУ імені В.Н.Каразіна |
Citation: | Two-stage one-pot interaction of acyclic β-ketoesters, DMFDMA and 2-cyanomethylbenzimidazole / M. A. Vodolazhenko, A. E. Mykhailenko, N. Yu. Gorobets, S. M. Desenko // Вісник Харківського національного університету. Серія Хімія. – 2017. – Вип. 29 (52). – Р. 31–45. |
Abstract: | A one-pot two-stage interaction of acyclic β-ketoesters, dimethylformamide dimethylacetal (DMFDMA) and 2-cyanomethylbenzimidazole was studied. Carried out under microwave irradiation in 2-propanol in the presence of piperidine, this transformation leads to the formation of 4-cyanobenzo[4,5]imidazo [1,2-α]pyridine-2-carboxylates, whereas at room temperature in methanol in the presence of sodium methylate 1-hydroxybenzo[4,5]imidazo[1,2-α]pyridine-4-carbonitriles are formed. Intermediate enamines initially formed from β-ketoesters and DMFDMA attack methylene group of 2-cyanomethylbenzimidazole followed by heterocyclizaton. In the presence of piperidine the benzimidazole nitrogen atom attacks the keto group of the β-ketoester fragment, whereas in the strong basic conditions cyclization occurs by the ester group. |
URI: | https://repo.knmu.edu.ua/handle/123456789/19212 |
Appears in Collections: | Наукові праці. Кафедра медичної та біоорганічної хімії |
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Two-stage one-pot interaction of acyclic β-ketoesters.pdf | 707,87 kB | Adobe PDF | View/Open |
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