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 Full article

Journal

Beilstein Journal of Organic Chemistry
ISSN: 1860-5397

Output data

Year: 2016, Volume: 12, Pages: 950-956 Pages count : 7 DOI: 10.3762/bjoc.12.93

Tags

alkynes; quinolinones; Friedel-Crafts reactions; superacids; superelectrophilic activation

Authors

Gurskaya Larisa Yu. ^1,2 , Belyanskaya Diana S. ¹ , Ryabukhin Dmitry S. ^1,3 , Nilov Denis I. ¹ , Boyarskaya Irina A. ¹ , Vasilyev Aleksander V. ^1,3

Affiliations

1	(Данные Web of science) St Petersburg State Univ, Inst Chem, Dept Organ Chem, Univ Skaya Nab 7-9, St Petersburg 199034, Russia
2	(Данные Web of science) Russian Acad Sci, NN Vorozhtsov Novosibirsk Inst Organ Chem, Siberian Branch, Ul Lavrentieva 9, Novosibirsk 630090, Russia
3	(Данные Web of science) St Petersburg State Forest Tech Univ, Dept Chem, Inst Per 5, St Petersburg 194021, Russia

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.

Gurskaya L.Y. , Belyanskaya D.S. , Ryabukhin D.S. , Nilov D.I. , Boyarskaya I.A. , Vasilyev A.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

Beilstein Journal of Organic Chemistry. 2016. V.12. P.950-956. DOI: 10.3762/bjoc.12.93 WOS Scopus РИНЦ

Full text from publisher

Published online:

May 11, 2016

Web of science	WOS:000375485900001
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