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DOI: 10.1055/s-0040-1705985
Regioselective Functionalization of N-Fused Heteroaromatics via FeCl3-Catalyzed Nucleophilic Addition to Activated N-Heterocycles
We thank the National Research Foundation of Korea (NRF-2018R1A6A1A03023718 and NRF-2020R1A2C2005961) for generous financial support.
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 synthesisSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1705985. Included are 1H and 13C NMR spectra of synthesized compounds and CIF files for 3a and 5a.
- Supporting Information
- CIF File
Publikationsverlauf
Eingereicht: 06. Oktober 2020
Angenommen nach Revision: 26. Oktober 2020
Artikel online veröffentlicht:
08. Dezember 2020
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For reviews, see:
For selected papers on biological studies of indolizine derivatives, see:
For selected reports on biological activities of pyrrolo[1,2-a]pyrazine derivatives, see:
For selected examples, see: