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

Chandran R.; Keshri Nath Tiwari

doi:10.1055/s-0040-1707816

Synthesis, Table of Contents

Synthesis 2020; 52(15): 2233-2240
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

Chandran R.

,

Keshri Nath Tiwari ∗

Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research (NIPER), Raebareli New Transit Campus, Bijnour-Sisendi Road, Lucknow 226002, India Email: keshri.tiwari@niperraebareli.edu.in

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Abstract

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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 - isatin

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References

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