4.4 Article

Iron-Catalyzed Synthesis of Pyrrolo[2,1-a]isoquinolines via 1,3-Dipolar Cycloaddition/Elimination/Aromatization Cascade and Modifications

Journal

SYNLETT
Volume 33, Issue 16, Pages 1645-1654

Publisher

GEORG THIEME VERLAG KG
DOI: 10.1055/a-1896-3512

Keywords

iron catalysis; pyrrolo[2,1-a]isoquinoline; tetrahydroisoquinoline; nitroolefin; dipolar cycloaddition

Funding

  1. National Natural Science Foundation of China [21502013, 21871035]

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An iron-catalyzed synthesis of pyrro-lo[2,1-a]isoquinoline derivatives has been developed, achieving highly functionalized products through a three-component cascade reaction. The obtained products can be easily modified to form structurally complex molecules with privileged frameworks.
We have developed an iron-catalyzed synthesis of pyrro-lo[2,1-a]isoquinoline derivatives with tetrahydroisoquinolines, arylacyl bromides, and nitroolefins. Highly functionalized pyrrolo[2,1-a]isoquinolines can be obtained in moderate to good yields through a three-component N-alkylationioxidative 1,3-dipolar cycloaddition/elimination/aromatization cascade. The obtained products in this study can be easily modified by easy chemical transformations to structurally complex molecules bearing privileged framework.

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