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| - Synthesis of Isoquinolines and Pyridines by the Palladium/Copper-Catalyzed Coupling and Cyclization of TerminalAcetylenes and Unsaturated Imines: The Total Synthesis ofDecumbenine B
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| - Monosubstituted isoquinolines and pyridines have been prepared in good to excellent yields viacoupling of terminal acetylenes with the tert-butylimines of o-iodobenzaldehydes and 3-halo-2-alkenals in the presence of a palladium catalyst and subsequent copper-catalyzed cyclization ofthe intermediate iminoalkynes. In addition, isoquinoline heterocycles have been prepared inexcellent yields via copper-catalyzed cyclization of iminoalkynes. The choice of cyclization conditionsis dependent upon the nature of the terminal acetylene that is employed, as only aryl and alkenylacetylenes cyclize under the palladium-catalyzed reaction conditions that have been developed.However, aryl-, vinylic-, and alkyl-substituted acetylenes undergo palladium-catalyzed couplingand subsequent copper-catalyzed cyclization in excellent yields. The total synthesis of theisoquinoline natural product decumbenine B has been accomplished in seven steps and 20% overallyield by employing this palladium-catalyzed coupling and cyclization methodology.
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