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.
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.
authors.affiliation: 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.
authors.forename: Larisa Yu
authors.initials: LY
authors.lastname: Gurskaya
authors.affiliation: Department of Organic Chemistry, Institute of Chemistry, Saint Petersburg State University, Universitetskaya nab., 7/9, Saint Petersburg, 199034, Russia.
authors.forename: Diana S
authors.initials: DS
authors.lastname: Belyanskaya
authors.affiliation: 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.
authors.forename: Dmitry S
authors.initials: DS
authors.lastname: Ryabukhin
authors.affiliation: Department of Organic Chemistry, Institute of Chemistry, Saint Petersburg State University, Universitetskaya nab., 7/9, Saint Petersburg, 199034, Russia.
authors.forename: Denis I
authors.initials: DI
authors.lastname: Nilov
authors.affiliation: Department of Organic Chemistry, Institute of Chemistry, Saint Petersburg State University, Universitetskaya nab., 7/9, Saint Petersburg, 199034, Russia.
authors.forename: Irina A
authors.initials: IA
authors.lastname: Boyarskaya
authors.affiliation: 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.
authors.forename: Aleksander V
authors.initials: AV
authors.lastname: Vasilyev
keywords: Friedel–Crafts reactions; alkynes; quinolinones; superacids; superelectrophilic activation