A ROUTE TO TRIAZOLE-FUSED SULTAMS VIA METAL-FREE BASE-MEDIATED CYCLIZATION OF SULFONAMIDE-TETHERED 5-IODOTRIAZOLES
Journal of Organic Chemistry. Том 85. 2020. С. 7863-7876
N-(Propargyl)indole-2-carbonitriles undergo DBU-catalyzed addition of CH-acids to nitriles, followed by cyclization to give 9-aminopyrido[1,2-a]indoles. The reaction proceeds through the initial formation of a push-pull enamine, alkyne-allene rearrangement and intramolecular nucleophilic cyclization. Nitromethane and malonate esters can be employed as the CH-acids. The resulting compounds were found to exhibit fluorescence properties. © 2020 The Royal Society of Chemistry.