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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| Series: | Beilstein Journal of Organic Chemistry |
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| Online Access: | https://doi.org/10.3762/bjoc.12.93 |
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doaj-771a98839bc84576bc7d91e4ce3954382021-03-02T10:05:02ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972016-05-0112195095610.3762/bjoc.12.931860-5397-12-93Reactions of N,3-diarylpropiolamides with arenes under superelectrophilic activation: synthesis of 4,4-diaryl-3,4-dihydroquinolin-2(1H)-ones and their derivativesLarisa Yu. Gurskaya0Diana S. Belyanskaya1Dmitry S. Ryabukhin2Denis I. Nilov3Irina A. Boyarskaya4Aleksander V. Vasilyev5Department of Organic Chemistry, Institute of Chemistry, Saint Petersburg State University, Universitetskaya nab., 7/9, Saint Petersburg, 199034, RussiaDepartment of Organic Chemistry, Institute of Chemistry, Saint Petersburg State University, Universitetskaya nab., 7/9, Saint Petersburg, 199034, RussiaDepartment of Organic Chemistry, Institute of Chemistry, Saint Petersburg State University, Universitetskaya nab., 7/9, Saint Petersburg, 199034, RussiaDepartment of Organic Chemistry, Institute of Chemistry, Saint Petersburg State University, Universitetskaya nab., 7/9, Saint Petersburg, 199034, RussiaDepartment of Organic Chemistry, Institute of Chemistry, Saint Petersburg State University, Universitetskaya nab., 7/9, Saint Petersburg, 199034, RussiaDepartment of Organic Chemistry, Institute of Chemistry, Saint Petersburg State University, Universitetskaya nab., 7/9, Saint Petersburg, 199034, RussiaThe 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.https://doi.org/10.3762/bjoc.12.93alkynesquinolinonesFriedel–Crafts reactionssuperacidssuperelectrophilic activation |
| collection |
DOAJ |
| language |
English |
| format |
Article |
| sources |
DOAJ |
| author |
Larisa Yu. Gurskaya Diana S. Belyanskaya Dmitry S. Ryabukhin Denis I. Nilov Irina A. Boyarskaya Aleksander V. Vasilyev |
| spellingShingle |
Larisa Yu. Gurskaya Diana S. Belyanskaya Dmitry S. Ryabukhin Denis I. Nilov Irina A. Boyarskaya Aleksander V. Vasilyev 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 alkynes quinolinones Friedel–Crafts reactions superacids superelectrophilic activation |
| author_facet |
Larisa Yu. Gurskaya Diana S. Belyanskaya Dmitry S. Ryabukhin Denis I. Nilov Irina A. Boyarskaya Aleksander V. Vasilyev |
| author_sort |
Larisa Yu. Gurskaya |
| 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_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_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_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 |
| publisher |
Beilstein-Institut |
| series |
Beilstein Journal of Organic Chemistry |
| issn |
1860-5397 |
| publishDate |
2016-05-01 |
| 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. |
| topic |
alkynes quinolinones Friedel–Crafts reactions superacids superelectrophilic activation |
| url |
https://doi.org/10.3762/bjoc.12.93 |
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