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One‐Pot Two‐Step Double Annulation of <i>N</i>‐Methoxybenzamides with Alkynes and Alkenes: Regioselective Construction of Isoindolo[2,1‐<i>b</i>]isoquinolin‐5(7<i>H</i>)‐ones

Praveen Kumar Naikawadi, Lingaswamy Mucherla, Rambabu Dandela, Madhavi Sambari, K. Shiva Kumar

2021Advanced Synthesis & Catalysis19 citationsDOI

Abstract

Abstract A one‐pot two‐step double annulation strategy to produce isoindolo[2,1‐ b ]isoquinolin‐5(7 H )‐ones via the reaction of N ‐methoxybenzamides with symmetrical/unsymmetrical alkynes and alkenes has been developed, which proceeds through Ru‐catalysed unsymmetrical double annulations using a single DG under single catalytic conditions. Furthermore, we have developed amide‐alkyne regioselective annulations using unsymmetrical internal alkynes having oxygen/nitrogen substituents leading to a single isomer. The developed procedure offers broad substrate scope, tolerates a wide range of functional groups and affords good product yields. magnified image

Topics & Concepts

AnnulationRegioselectivityChemistryAmideAlkyneSubstrate (aquarium)Combinatorial chemistryCatalysisStereochemistryMedicinal chemistryOrganic chemistryGeologyOceanographyCatalytic C–H Functionalization MethodsSynthetic Organic Chemistry MethodsSynthesis and Catalytic Reactions
One‐Pot Two‐Step Double Annulation of <i>N</i>‐Methoxybenzamides with Alkynes and Alkenes: Regioselective Construction of Isoindolo[2,1‐<i>b</i>]isoquinolin‐5(7<i>H</i>)‐ones | Litcius