One-Step Synthesis\nof\n2‑Arylquinolin-4(1<i>H</i>)‑Ones from 1‑(2-Aminoaryl)-3-Arylpropan-1-Ones\nvia Pd(II)-Catalyzed Dehydrogenative Cyclization

In\nthis study, we developed palladium-catalyzed dehydrogenative\ncyclization to transform 1-(2-aminoaryl)-3-arylpropan-1-ones into\n2-arylquinolin-4(1<i>H</i>)-ones, also known as aza-flavones\nwhich are the bioisosteres of flavones, in an atom-economic manner.\nThis method exhibited excellent chemical compatibility with a broad\nsubstrate scope, accommodating up to 25 derivatives. Additionally,\nkinetic studies were performed to elucidate the reaction mechanism.\nFurther, 2-phenylquinolin-4(1<i>H</i>)-one was used as a\ncommon intermediate for synthesizing privileged structures such as\n4-methoxyquinoline, <i>N</i>-methylquinoline-4(1<i>H</i>)-one, and 4-(pseudo)halogenated quinoline moieties.

Publication Details

Journal
Figshare
Published
2024-12-31
DOI
https://doi.org/10.1021/acs.joc.4c01901.s001
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
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article

One-Step Synthesis\nof\n2‑Arylquinolin-4(1H)‑Ones from 1‑(2-Aminoaryl)-3-Arylpropan-1-Ones\nvia Pd(II)-Catalyzed Dehydrogenative Cyclization

Figshare
Catalytic C–H Functionalization Methods
article

One-Step Synthesis\nof\n2‑Arylquinolin-4(1H)‑Ones from 1‑(2-Aminoaryl)-3-Arylpropan-1-Ones\nvia Pd(II)-Catalyzed Dehydrogenative Cyclization

article en

Abstract

In\nthis study, we developed palladium-catalyzed dehydrogenative\ncyclization to transform 1-(2-aminoaryl)-3-arylpropan-1-ones into\n2-arylquinolin-4(1<i>H</i>)-ones, also known as aza-flavones\nwhich are the bioisosteres of flavones, in an atom-economic manner.\nThis method exhibited excellent chemical compatibility with a broad\nsubstrate scope, accommodating up to 25 derivatives. Additionally,\nkinetic studies were performed to elucidate the reaction mechanism.\nFurther, 2-phenylquinolin-4(1<i>H</i>)-one was used as a\ncommon intermediate for synthesizing privileged structures such as\n4-methoxyquinoline, <i>N</i>-methylquinoline-4(1<i>H</i>)-one, and 4-(pseudo)halogenated quinoline moieties.

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Catalytic C–H Functionalization Methods
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