Facile Synthesis of Fully Substituted Dihydro-β-Carbolines via Br(o)nsted Acid Promoted Cascade Reac

来源 :The 24th International Society of Heterocyclic Chemistry Con | 被引量 : 0次 | 上传用户:gratify
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In the course of our studies on gold-catalyzed cascade transformations of indolyl tethered alkynes,[1-4] we found a straightforward synthesis of fully-substituted β-carbolines via Br(o)nsted acid promoted cyclizations of α-indolyl propargylic alcohols with nitrones.The use of nitrones bearing alkenyl or electron rich aryl groups as R4 substituent dramatically switches the reaction pathway to afford tetrasubstituted aikenes and amines, which is assumed to proceed through an rearrangement reaction involving N-O bond cleavage and 1,2-migration of R4 group to an adjacent nitrogen atom.
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