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Reactions of N,3-diarylpropiolamides with arenes under superelectrophilic activation: synthesis of 4,4-diaryl-3,4-dihydroquinolin-2(1H)-ones and their derivatives
Publication type: Journal Article
Publication date: 2016-05-11
scimago Q2
wos Q3
SJR: 0.482
CiteScore: 3.8
Impact factor: 2.1
ISSN: 18605397
PubMed ID:
27340485
Organic Chemistry
Abstract
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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Belyanskaya D. S. et al. Reactions of N,3-diarylpropiolamides with arenes under superelectrophilic activation: synthesis of 4,4-diaryl-3,4-dihydroquinolin-2(1H)-ones and their derivatives // Beilstein Journal of Organic Chemistry. 2016. Vol. 12. pp. 950-956.
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Belyanskaya D. S., Nilov D. I., Boyarskaya I. A. Reactions of N,3-diarylpropiolamides with arenes under superelectrophilic activation: synthesis of 4,4-diaryl-3,4-dihydroquinolin-2(1H)-ones and their derivatives // Beilstein Journal of Organic Chemistry. 2016. Vol. 12. pp. 950-956.
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TY - JOUR
DO - 10.3762/bjoc.12.93
UR - https://doi.org/10.3762/bjoc.12.93
TI - Reactions of N,3-diarylpropiolamides with arenes under superelectrophilic activation: synthesis of 4,4-diaryl-3,4-dihydroquinolin-2(1H)-ones and their derivatives
T2 - Beilstein Journal of Organic Chemistry
AU - Belyanskaya, Diana S
AU - Nilov, Denis I
AU - Boyarskaya, Irina A
PY - 2016
DA - 2016/05/11
PB - Beilstein-Institut
SP - 950-956
VL - 12
PMID - 27340485
SN - 1860-5397
ER -
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@article{2016_Belyanskaya,
author = {Diana S Belyanskaya and Denis I Nilov and Irina A Boyarskaya},
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},
journal = {Beilstein Journal of Organic Chemistry},
year = {2016},
volume = {12},
publisher = {Beilstein-Institut},
month = {may},
url = {https://doi.org/10.3762/bjoc.12.93},
pages = {950--956},
doi = {10.3762/bjoc.12.93}
}
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