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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Autores principales: Gurskaya, Larisa Yu, Belyanskaya, Diana S, Ryabukhin, Dmitry S, Nilov, Denis I, Boyarskaya, Irina A, Vasilyev, Aleksander V
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2016
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4901988/
https://www.ncbi.nlm.nih.gov/pubmed/27340485
http://dx.doi.org/10.3762/bjoc.12.93
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author Gurskaya, Larisa Yu
Belyanskaya, Diana S
Ryabukhin, Dmitry S
Nilov, Denis I
Boyarskaya, Irina A
Vasilyev, Aleksander V
author_facet Gurskaya, Larisa Yu
Belyanskaya, Diana S
Ryabukhin, Dmitry S
Nilov, Denis I
Boyarskaya, Irina A
Vasilyev, Aleksander V
author_sort Gurskaya, Larisa Yu
collection PubMed
description 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.
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spelling pubmed-49019882016-06-23 Reactions of N,3-diarylpropiolamides with arenes under superelectrophilic activation: synthesis of 4,4-diaryl-3,4-dihydroquinolin-2(1H)-ones and their derivatives Gurskaya, Larisa Yu Belyanskaya, Diana S Ryabukhin, Dmitry S Nilov, Denis I Boyarskaya, Irina A Vasilyev, Aleksander V Beilstein J Org Chem Full Research Paper 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. Beilstein-Institut 2016-05-11 /pmc/articles/PMC4901988/ /pubmed/27340485 http://dx.doi.org/10.3762/bjoc.12.93 Text en Copyright © 2016, Gurskaya et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Gurskaya, Larisa Yu
Belyanskaya, Diana S
Ryabukhin, Dmitry S
Nilov, Denis I
Boyarskaya, Irina A
Vasilyev, Aleksander V
Reactions of N,3-diarylpropiolamides with arenes under superelectrophilic activation: synthesis of 4,4-diaryl-3,4-dihydroquinolin-2(1H)-ones and their derivatives
title Reactions of N,3-diarylpropiolamides with arenes under superelectrophilic activation: synthesis of 4,4-diaryl-3,4-dihydroquinolin-2(1H)-ones and their derivatives
title_full Reactions of N,3-diarylpropiolamides with arenes under superelectrophilic activation: synthesis of 4,4-diaryl-3,4-dihydroquinolin-2(1H)-ones and their derivatives
title_fullStr Reactions of N,3-diarylpropiolamides with arenes under superelectrophilic activation: synthesis of 4,4-diaryl-3,4-dihydroquinolin-2(1H)-ones and their derivatives
title_full_unstemmed Reactions of N,3-diarylpropiolamides with arenes under superelectrophilic activation: synthesis of 4,4-diaryl-3,4-dihydroquinolin-2(1H)-ones and their derivatives
title_short Reactions of N,3-diarylpropiolamides with arenes under superelectrophilic activation: synthesis of 4,4-diaryl-3,4-dihydroquinolin-2(1H)-ones and their derivatives
title_sort reactions of n,3-diarylpropiolamides with arenes under superelectrophilic activation: synthesis of 4,4-diaryl-3,4-dihydroquinolin-2(1h)-ones and their derivatives
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4901988/
https://www.ncbi.nlm.nih.gov/pubmed/27340485
http://dx.doi.org/10.3762/bjoc.12.93
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