Product structure in the reaction of dimethyl acetylenedicarboxylate with 2-furyl-1,2,3,4-tetrahydroquinolines

Advances in the Chemistry of Tetrahydroquinolines

“…N -Acylation of compounds 699 with acryloyl chloride in the presence of triethylamine afforded the corresponding, nonisolated, N -acyl intermediate A , which subsequently underwent a [4 + 2] intramolecular cycloaddition reaction with the furyl diene to give compounds 700 ; their treatment with phosphoric acid provided the tetracyclic compounds 701 through a ring-opening-aromatization sequence (Scheme ). A similar strategy was subsequently described by Zubkov and co-workers …”

“…A similar strategy was subsequently described by Zubkov and coworkers. 675 The tetrahydroquinoline-fused benzodiazepine 704 was prepared from the readily available tetrahydroquinoline derivative 702, the key step being the cyanation at C-2 position under electrochemical conditions. 676 The benzodiazepine N-oxide 703 was obtained in two successive electrochemical reactions, that is, 2-cyanation and partial reduction of the nitro group followed by intramolecular cyclization.…”

Crystal structure and Hirshfeld surface analysis of N-[2-(5-methylfuran-2-yl)phenyl]-3-nitro-N-[(3-nitrophenyl)sulfonyl]benzenesulfonamide

“…1), which is possible only with the use of strong bases (Bartsch et al, 1977;Li et al, 2022). The obtained product can serve as a compound for studying furan fragment-opening (Pilipenko et al, 2012;Butin et al, 2006) or the Diels-Alder reactions of furans (Borisova et al, 2018a,b;Krishna et al, 2022;Zubkov et al, 2007) and for studying biological activity. On the other hand, intermolecular noncovalent interactions organize the molecular aggregates, catalytic intermediates, etc., which play a critical role in the functional properties of heterocyclic compounds (Gurbanov et al, 2020a(Gurbanov et al, ,b, 2022Ma et al, 2021;Mahmoudi, et al, 2017a,b;Mahmudov et al, 2011Mahmudov et al, , 2022.…”

The Povarov Reaction: A Versatile Method to Synthesize Tetrahydroquinolines, Quinolines and Julolidines

“…Regarding the reaction medium, various polar and non-polar solvents have been explored, for example, acetonitrile, 2 4 6 , 22 23 24 , 36 37 38 THF, 159 161 DMSO, 160 162 163 166 173 ethanol, 146 , 181 182 183 DMF, 158 acetic acid, 157 dichloromethane, 97 138 145 148 150 179 180 184 TFE, 137 152 diethyl ether, 185 dichloroethane, 140 142 151 153 165 186 chloroform 174 and toluene. 147 171 177 Greener alternatives were also reported such as the absence of a solvent 84 149 174 176 178 or the use of a DES (Scheme 13 ).…”