Work

Synthesis of Multifunctional 2,3‐Dihydroquinolin‐4(1 H )‐one Building Blocks via Permanganate‐Promoted Oxidation of 1,2,3,4‐Tetrahydroquinolines

Year: 2026

Type: article

Abstract: A practical and scalable method for the preparation of 2,3-dihydroquinolin-4(1H)-one derivatives has been developed via selective benzylic oxidation of N-acyl-protected 1,2,3,4-tetrahydroquinolines using aqueous KMnO₄. The optimized oxidation protocol demonstrates excellent functional-group tolerance toward halogen, nitro, and methoxy substituents and proceeds efficiently on multi-gram scale (up to 20 g) without erosion in yield. The synthetic versatility of the obtained quinolinones was further demonstrated through their transformation into diverse bifunctional building blocks, including mono-N-Boc diamines bearing either exocyclic or endocyclic protected nitrogen atoms, aryl- and vinylboronates.

Source: ChemistrySelect

DOI: 10.1002/slct.202507236

Authors: Viktor Yakubovskyi, Olena Semoshkina, Kostiantyn Melnykov, Oleksandr O. Grygorenko, Oleksandr S. Liashuk

Institutions: Taras Shevchenko National University of Kyiv, Enamine (Ukraine)

Language: English

Topic: Oxidative Organic Chemistry Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funder: Ministry of Education and Science of Ukraine

Award: G2979084016