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SM ISO690:2012 SUCMAN, Natalia. Nucleophilic addition of pyridine amines to the double bond of in situ generated morita-baylis-hillman adducts from indole-2,3-dione. In: New frontiers in natural product chemistry, Ed. 7, 12-13 octombrie 2023, Chișinău. Chișinău, Republica Moldova: Tipografia "Artpoligraf", 2023, Ediția 7, p. 26. DOI: https://doi.org/10.19261/nfnpc.2023.ab19 |
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New frontiers in natural product chemistry Ediția 7, 2023 |
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Conferința " New frontiers in natural product chemistry." 7, Chișinău, Moldova, 12-13 octombrie 2023 | |||||||
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DOI:https://doi.org/10.19261/nfnpc.2023.ab19 | |||||||
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This report will present the results of addition reactions of indole-2,3-dione to methyl or nitryl acrylate and amino-methyl-pyridine. The addition of an activated alkene like methyl acrylate and nitryl acrylate to a carbon electrophile in the presence of a nucleophilic catalyst is named Morita-Bailys Hillman (MBH) addition. Such adducts are very popular in organic chemistry [1-3]. As a result of screening various substances in search of new catalysts in MBH reactions, substances were discovered that not only catalyzed the addition of olefin to a carbonyl compound but also acted as a reagent themselves, leading to the formation of fundamentally new substances (Figure 1). After analyzing NMR spectra, conclusions were drawn about the structure of the substance, which was subsequently confirmed by X-ray structural analysis. Figure 1. General scheme of nucleophilic addition of pyridine amines to the double bond of in situ generated Morita-Baylis-Hillman adducts It should be noted that methyl acrylate reacts better under these conditions, and the reaction proceeds faster than acrylonitrile. In all cases, the yield was around 70%, and the reaction proceeded regioselectively, forming only one diastereomeric pair of enantiomers. It is also worth noting that the complex ether product hydrolyzes during the reaction, forming the corresponding acid. Even when the reaction is carried out under practically absolute conditions, up to 30% of the final product yield is attributed to the acid. |
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