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Gold-Catalyzed Bicyclic Annulations of N-(o-Alkynylphenyl)imines with α-Diazo Esters to Form 5,6-Dihydroindolo[2,1-a]isoquinolines.

One-pot synthesis of 5,6-dihydroindolo[2,1-a]isoquinolines from gold-catalyzed annulations between N-(o-alkynylphenyl)imines and α-diazo esters is described. This cascade reaction involves an initial attack of the diazo ester at the imine to form… Click to show full abstract

One-pot synthesis of 5,6-dihydroindolo[2,1-a]isoquinolines from gold-catalyzed annulations between N-(o-alkynylphenyl)imines and α-diazo esters is described. This cascade reaction involves an initial attack of the diazo ester at the imine to form cis-aziridine, followed by stereoselective [3 + 3]-annulations with the tethered arylalkyne. We have employed this new catalysis to prepare one bioactive 5,6-dihydroindolo[2,1-a]isoquinoline molecule.

Keywords: dihydroindolo isoquinolines; imines diazo; alkynylphenyl imines; annulations alkynylphenyl; diazo esters; gold catalyzed

Journal Title: Organic letters
Year Published: 2022

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