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Krapcho Dealkoxycarbonylation Strategy of Ethyl Cyanoacetate for the Synthesis of 3-Hydroxy-3-cyanomethyl-2-oxindoles and 3,3′-Dicyanomethyl-2-oxindoles in a Reaction with Isatin
Synthesis ( IF 2.2 ) Pub Date : 2020-05-25 , DOI: 10.1055/s-0040-1707816 Keshri Nath Tiwari 1 , Chandran R.
Synthesis ( IF 2.2 ) Pub Date : 2020-05-25 , DOI: 10.1055/s-0040-1707816 Keshri Nath Tiwari 1 , Chandran R.
Affiliation
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A new strategy for the synthesis of 3-hydroxy-3-cyanomethyl-2-oxindoles and 3,3′-dicyanomethyl-2-oxindoles in a reaction of isatin with ethyl cyanoacetate by Krapcho dealkoxycarbonylation reaction in aqueous media is demonstrated. The reaction provides an easy access to synthetically and medicinally valuable oxindole alkylnitriles in good to very good yields. Wider substrate scope and operationally simple experimental procedures are highlighted features of the developed protocol. Based on control experiments, a plausible mechanism of reaction and synergistic effect of water is also rationalized.
中文翻译：
氰基乙酸乙酯的Krapcho脱氧羰基化反应策略，用于与Isatin反应合成3-Hydroxy-3-cyanomethyl-2-oxindoles和3,3'-Dicyanomethyl-2-oxindoles
提出了一种在水性介质中通过Krapcho脱氧羰基羰基化反应在靛红与氰基乙酸乙酯反应中合成3-羟基-3-氰基甲基-2-氧吲哚和3,3'-二氰基甲基-2-氧吲哚的新策略。该反应提供了易于获得的合成和医学上有价值的羟吲哚烷基腈，收率很高。较宽的基板范围和操作简单的实验程序是已开发协议的突出特点。在控制实验的基础上，合理化了水的反应机理和协同效应。
更新日期：2020-05-25
中文翻译：
氰基乙酸乙酯的Krapcho脱氧羰基化反应策略，用于与Isatin反应合成3-Hydroxy-3-cyanomethyl-2-oxindoles和3,3'-Dicyanomethyl-2-oxindoles
提出了一种在水性介质中通过Krapcho脱氧羰基羰基化反应在靛红与氰基乙酸乙酯反应中合成3-羟基-3-氰基甲基-2-氧吲哚和3,3'-二氰基甲基-2-氧吲哚的新策略。该反应提供了易于获得的合成和医学上有价值的羟吲哚烷基腈，收率很高。较宽的基板范围和操作简单的实验程序是已开发协议的突出特点。在控制实验的基础上，合理化了水的反应机理和协同效应。
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