Synthesis of 1,2-Dihydroquinolines via Hydrazine-Catalyzed Ring-Closing Carbonyl-Olefin Metathesis
Yunfei Zhang, Jae Hun Sim, Samantha N. MacMillan, Tristan H. Lambert
Abstract
The synthesis of 1,2-dihydroquinolines by the hydrazine-catalyzed ring-closing carbonyl-olefin metathesis (RCCOM) of N-prenylated 2-aminobenzaldehydes is reported. Substrates with a variety of substitution patterns are shown. With an acid-labile protecting group on the nitrogen atom, in situ deprotection and autoxidation furnish quinoline. In comparison with related oxygen-containing substrates, the cycloaddition step of the catalytic cycle is shown to be slower, but the cycloreversion is found to be more facile.
Topics & Concepts
ChemistryHydrazine (antidepressant)CatalysisOlefin fiberAutoxidationRing (chemistry)QuinolineOrganic chemistryOlefin metathesisRing-closing metathesisMetathesisCombinatorial chemistryMedicinal chemistryPolymerizationPolymerChromatographySynthetic Organic Chemistry MethodsChemical Synthesis and AnalysisAsymmetric Synthesis and Catalysis