One-Pot Synthesis of <i>N</i>-Fused Benzimidazo-β-carbolines through Sequential Propargylation/<i>aza</i>-Cycloisomerization Approach
Chada Raji Reddy, Karna Nair, Ejjirotu Srinivasu, Muppidi Subbarao, René Grée
Abstract
The first sequential acid-catalyzed propargylation/base-mediated aza -cycloisomerization between indolyl-benzimidazoles and propargylic alcohols is described. This protocol enables the one-pot construction of N -fused benzimidazo-β-carbolines in good yields. The synthetic utility of this approach is demonstrated by the assembly of an aza -helicene and also by a gram-scale reaction.
Topics & Concepts
CycloisomerizationHeliceneChemistryCombinatorial chemistryBase (topology)CatalysisOrganic chemistryMoleculeMathematicsMathematical analysisSynthesis and bioactivity of alkaloidsCatalytic Alkyne ReactionsSynthesis of Indole Derivatives