Regioselective House–Meinwald rearrangement in oxindoles: access to substituted quinolinones

Organic & Biomolecular Chemistry 2026

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Authors: Mohan Banyangala, K. S. Sandhya, Ramakrishnan Thushara, Athira Chithralekha Santhoshkumar, Liyo Vincent K, Cherumuttathu Hariharan Suresh, Jayamurthy Purushothaman, Sasidhar B. Somappa
DOI: 10.1039/d6ob00128a
Cited by: 1
References: 32

Abstract

House-Meinwald rearrangement of oxindole substrates facilitating a one-pot synthesis of 3-substituted 4-hydroxyquinolin-2-ones and quinoline-2,4-diones under EBHP and base-mediated conditions is reported. This transformation proceeds through a well-defined sequence involving epoxidation, formation of a quinone methide-type intermediate, and subsequent ring expansion. The crucial carbonyl migration step was further substantiated by DFT studies. Moreover, the synthetic utility of the resulting 3-substituted 4-hydroxyquinolin-2-ones was demonstrated through late-stage diversification, highlighting the versatility of this protocol.

Fields of Study & Subjects

Organic and Inorganic Chemical Reactions Synthesis and Biological Activity Synthesis of heterocyclic compounds

Publication details

Journal / source
Organic & Biomolecular Chemistry
Publisher
Royal Society of Chemistry (RSC)
Volume
24
Issue
10
Pages
2028–2033
Publication date
1 January 2026
Language
EN