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

Larisa Yu Gurskaya; Diana S Belyanskaya; Dmitry S Ryabukhin; Denis I Nilov; Irina A Boyarskaya; Aleksander V Vasilyev

doi:10.3762/bjoc.12.93

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 J Org Chem. 2016 May 11:12:950-6. doi: 10.3762/bjoc.12.93. eCollection 2016.

Authors

Larisa Yu Gurskaya¹, Diana S Belyanskaya², Dmitry S Ryabukhin³, Denis I Nilov², Irina A Boyarskaya², Aleksander V Vasilyev³

Affiliations

¹ Department of Organic Chemistry, Institute of Chemistry, Saint Petersburg State University, Universitetskaya nab., 7/9, Saint Petersburg, 199034, Russia; N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of Russian Academy of Science, ul. Lavrentieva 9, Novosibirsk, 630090, Russia.
² Department of Organic Chemistry, Institute of Chemistry, Saint Petersburg State University, Universitetskaya nab., 7/9, Saint Petersburg, 199034, Russia.
³ Department of Organic Chemistry, Institute of Chemistry, Saint Petersburg State University, Universitetskaya nab., 7/9, Saint Petersburg, 199034, Russia; Department of Chemistry, Saint Petersburg State Forest Technical University, Institutsky per. 5, Saint Petersburg, 194021, Russia.

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.

Keywords: Friedel–Crafts reactions; alkynes; quinolinones; superacids; superelectrophilic activation.