Synthesis of functionalised 2,3-dihydroquinolin-4(1: H)-ones vs. quinoline or N -alkenylindole derivatives through sequential reactions of 2-alkynylanilines with ketones

Vincenzo Marsicano, Antonio Arcadi, Marco Chiarini, Giancarlo Fabrizi, Antonella Goggiamani, Antonia Iazzetti

Risultato della ricerca: Contributo in rivistaArticolo in rivista

Abstract

This study describes diversity-oriented synthesis of 2,2,3-substituted-2,3-dihydroquinolin-4(1H)-ones vs. functionalised quinoline or N-alkenylindole derivatives through Brønsted acid mediated or Lewis acid catalyzed sequential reactions of 2-alkynylanilines with ketones. In particular, a series of challenging quinolin-4-one derivatives are prepared with good functional group tolerance in an atom-economical fashion by using p-toluenesulfonic acid monohydrate as a promoter of the reaction of ketones with 2-alkynylanilines in EtOH at reflux, while the same starting materials give the corresponding 4-substituted quinolines in toluene at 110 °C both in the presence of p-toluenesulfonic acid monohydrate as the promoter and FeCl3 as the catalyst. The divergent formation of N-alkenylindole derivatives occurs by switching to the use of ZnBr2 as the catalyst under the same reaction conditions. Conversely, only 4-methylsubstituted quinoline derivatives were isolated by reacting 2-ethynylanilines and/or 2-trimethylsylilanilines with ketones in all examined cases. This journal is
Lingua originaleEnglish
pagine (da-a)421-438
Numero di pagine18
RivistaORGANIC & BIOMOLECULAR CHEMISTRY
Volume19
DOI
Stato di pubblicazionePubblicato - 2021

Keywords

  • N-alkenylindole, quinolines, quinolones, diversity-oriented synthesis

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