ChemInform Abstract: Product Structure in the Reaction of Dimethyl Acetylenedicarboxylate with 2‐Furyl‐1,2,3,4‐tetrahydroquinolines.

Abstract

Quinoline derivatives R 0410Product Structure in the Reaction of Dimethyl Acetylenedicarboxylate with 2-Furyl-1,2,3,4-tetrahydroquinolines. -(ZUBKOV, F. I.; ZAITSEV, V. P.; ORLOVA, A. A.; PEREGUDOV, A. S.; MIKHAILOVA, N. M.; VARLAMOV, A. V.; Russ.

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

“…Regarding the reaction medium, various polar and nonpolar 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).…”

Synthesis and oxidation of 2-furyl-4-R-substituted and furo[3,2-c]-condensed 1,2,3,4-tetrahydro-1,10-phenanthrolines and quinolines*

“…2 -Furyltetrahydroquinolines 2a,b, 3, and 4 used as the starting compounds in this work were obtained by the Povarov reaction from the corresponding furfurylideneanilines 1a,b and electron-rich alkenes (dihydrofuran, 3,4-2H-dihydropyran, and N-vinyl-2-pyrrolidone) in the presence of boron trifluoride etherate as described in our previous work [8]. The hydrogenated quinolines 2-4 are cis addition adducts.…”

“…This paucity is related primarily to the acidophobic nature of the furan fragment and, secondarily, to passivation of the acid catalysts. The behavior of 2-furyltetrahydroquinolines in the presence of oxidizing agents has also not been studied extensively and apparently is complex.2 -Furyltetrahydroquinolines 2a,b, 3, and 4 used as the starting compounds in this work were obtained by the Povarov reaction from the corresponding furfurylideneanilines 1a,b and electron-rich alkenes (dihydrofuran, 3,4-2H-dihydropyran, and N-vinyl-2-pyrrolidone) in the presence of boron trifluoride etherate as described in our previous work [8]. The hydrogenated quinolines 2-4 are cis addition adducts.…”