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Synlett 2025; 36(17): 2925-2929
DOI: 10.1055/s-0043-1775460
letter
Small Molecules in Medicinal Chemistry

A Novel Strategy for the Synthesis of N-Alkylated Oxindoles

Authors

  • Nguyen Duc Thien

    a   Hanoi University of Pharmacy, 13-15 Le Thanh Tong, Hanoi, 100000, Vietnam

  • Hoang Kim Ngoc

    a   Hanoi University of Pharmacy, 13-15 Le Thanh Tong, Hanoi, 100000, Vietnam

  • Nguyen-Hai Nam

    a   Hanoi University of Pharmacy, 13-15 Le Thanh Tong, Hanoi, 100000, Vietnam

  • Duong Tien Anh∗

    a   Hanoi University of Pharmacy, 13-15 Le Thanh Tong, Hanoi, 100000, Vietnam

  • Daniel Baecker  ∗

    b   Department of Pharmaceutical and Medicinal Chemistry, Institute of Pharmacy, Freie Universität Berlin, Königin-Luise-Straße 2+4, 14195 Berlin, Germany
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Abstract

The synthesis of N-alkylated oxindoles remains an important focus in organic chemistry, due to their common occurrence in bioactive compounds and pharmaceutical agents. An efficient novel strategy for alkylating the oxindole scaffold at the N-1 position is described. By using (N-methylpyrrol-2-yl)methylidene as a protecting group for the competing C-3 position, this methodology provides a simple and mild procedure to convert various oxindoles into their corresponding N-alkylated and N-benzylated derivatives in moderate to good overall yields (up to 67%).

Key words

oxindoles - alkylation - regiochemistry - protecting group

Supporting Information



Publication History

Received: 23 December 2024

Accepted after revision: 27 February 2025

Article published online:
08 April 2025

© 2025. Thieme. All rights reserved

Georg Thieme Verlag KG
Oswald-Hesse-Straße 50, 70469 Stuttgart, Germany

 

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