A Facile Method for the Synthesis of 3-Alkyloxindole

Tai-Ping      Du; Gang-Guo      Zhu; Jian      Zhou

doi:10.2174/157017812800167420

Abstract

Benzylamine in combination with acetic acid was identified as a powerful catalyst for the condensation of oxindole with aldehydes, acetone or cyclic ketones. A variety of 3-alkyloxindoles could be readily prepared in 10 mmol scale via the sequential benzylamine acetate catalyzed condensation of oxindoles with aldehydes (or ketones) and conjugate reduction by NaBH4.

Keywords: 3-alkenyloxindoles, 3-alkyloxindoles, benzylamine, conjugate reduction, carbonyl compounds, Knoevenagel condensations, alkylation, oxindoles, amination, arylation

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Letters in Organic Chemistry

Title: A Facile Method for the Synthesis of 3-Alkyloxindole

Volume: 9 Issue: 3

Author(s): Tai-Ping Du, Gang-Guo Zhu and Jian Zhou

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Keywords: 3-alkenyloxindoles, 3-alkyloxindoles, benzylamine, conjugate reduction, carbonyl compounds, Knoevenagel condensations, alkylation, oxindoles, amination, arylation

Abstract: Benzylamine in combination with acetic acid was identified as a powerful catalyst for the condensation of oxindole with aldehydes, acetone or cyclic ketones. A variety of 3-alkyloxindoles could be readily prepared in 10 mmol scale via the sequential benzylamine acetate catalyzed condensation of oxindoles with aldehydes (or ketones) and conjugate reduction by NaBH4.

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Du Tai-Ping, Zhu Gang-Guo and Zhou Jian, A Facile Method for the Synthesis of 3-Alkyloxindole, Letters in Organic Chemistry 2012; 9 (3) . https://dx.doi.org/10.2174/157017812800167420