Synthesis of 2-Functionalized 4-(Diethoxyphosphorylmethyl)-5-(1-bromoalkyl)furans and Their Reactions with Amines |
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Authors: | L. M. Pevzner |
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Affiliation: | (1) Russian Research Institute of Hydrolysis of Vegetable Materials, St. Petersburg, Russia |
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Abstract: | Phosphorylation of esters and nitriles of 4-chloromethyl-5-alkylfuran-2-carboxylic acids with triethyl phosphite yields the corresponding phosphonates. These compounds are brominated with N-bromosuccinimide in carbon tetrachloride at the α-position of the alkyl radical. The resulting 2-(1-bromoethyl)-, 2-(1-bromopropyl)-, and 2-(1-bromoisobutyl)furans react with secondary amines following the scheme of nucleophilic substitution. The dehydrobromination product was isolated only in the reaction of ethyl 4-(diethoxyphosphorylmethyl)-5-(1-bromoisopropyl)furan-2-carboxylate with triethylamine, but its yield was low. The reactions of bromo phosphonates with lithium carbonate in DMF result in their decomposition.__________Translated from Zhurnal Obshchei Khimii, Vol. 75, No. 5, 2005, pp. 820–828.Original Russian Text Copyright © 2005 by Pevzner. |
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