Reactions of N,3-diarylpropiolamides with arenes under superelectrophilic activation: synthesis of 4,4-diaryl-3,4-dihydroquinolin-2(1H)-ones and their derivatives

Reactions of N,3-diarylpropiolamides with arenes under superelectrophilic activation: synthesis of 4,4-diaryl-3,4-dihydroquinolin-2(1H)-ones and their derivatives

The reaction of 3-aryl-N-(aryl)propiolamides with arenes in TfOH at room temperature for 0.5 h led to 4,4-diaryl-3,4-dihydroquinolin-2-(1H)-ones in yields of 44–98%. The obtained dihydroquinolinones were further transformed into the corresponding N-acyl or N-formyl derivatives. For the latter, the s...

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Bibliographic Details
Main Authors: Larisa Yu. Gurskaya, Diana S. Belyanskaya, Dmitry S. Ryabukhin, Denis I. Nilov, Irina A. Boyarskaya, Aleksander V. Vasilyev
Format: Article
Language:English
Published: Beilstein-Institut 2016-05-01
Series:Beilstein Journal of Organic Chemistry
Subjects:
alkynes
quinolinones
Friedel–Crafts reactions
superacids
superelectrophilic activation
Online Access:https://doi.org/10.3762/bjoc.12.93
Description
Summary:The reaction of 3-aryl-N-(aryl)propiolamides with arenes in TfOH at room temperature for 0.5 h led to 4,4-diaryl-3,4-dihydroquinolin-2-(1H)-ones in yields of 44–98%. The obtained dihydroquinolinones were further transformed into the corresponding N-acyl or N-formyl derivatives. For the latter, the superelectrophilic activation of the N-formyl group by TfOH in the reaction with benzene resulted in the formation of N-(diphenylmethyl)-substituted dihydroquinolinones.
ISSN:1860-5397

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