Regioselective Functionalization of N-Fused Heteroaromatics via FeCl₃-Catalyzed Nucleophilic Addition to Activated N-Heterocycles

Abstract

Broadening of nitrogen-fused heteroaromatic chemical space such as indolizine and pyrrolo[1,2-a]pyrazine was achieved via FeCl­₃-catalyzed nucleophilic addition of these N-fused aromatic compounds to a wide range of azolinium systems generated in situ, leading to novel N-fused heteroaromatic scaffolds with dearomatized N-heterocyclic substituents regioselectively. Nucleophilic addition of indolizines and pyrrolo[1,2-a]pyrazines mainly occurred at the C1 position of the isoquinoliniums and at the C4 site of the quinoliniums.

Keywords

chemical space - indolizines - pyrrolo[1,2-a]pyrazines - dearomatization - nucleophilic addition - three-component reaction - diversity­-oriented synthesis

Publication History

Received: 06 October 2020

Accepted after revision: 26 October 2020

Article published online:
08 December 2020

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