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Synthesis 2020; 52(15): 2233-2240
DOI: 10.1055/s-0040-1707816
DOI: 10.1055/s-0040-1707816
paper
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
Further Information
Publication History
Received: 22 December 2019
Accepted after revision: 30 April 2020
Publication Date:
25 May 2020 (online)
Abstract
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.
Key words
aldol-type cyanomethylation - dealkoxycarbonylation - 3,3′-disubstituted oxindole - ethyl cyanoacetate - isatinSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1707816.
- Supporting Information
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