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A mild nitration of pyrrolo[2,1‐a]isoquinolines has been reached using sodium nitrite as nitro source in HFIP at ambient temperature. A variety of nitro‐bearing pyrrolo[2,1‐a]isoquinoline derivatives has been efficiently prepared in poor to quantitative yields (28–98 %). These products can be easily transformed to primary amines and amide by simple chemical reactions. Treatment of other nitrogen‐containing heterocycles such as pyrrolo[1,2‐a]quinoline and substituted indoles under this developed reaction system afforded nitro‐bearing N‐heterocycles in relatively lower yields (15–19 %). [ABSTRACT FROM AUTHOR]

We have developed an iron-catalyzed synthesis of pyrrolo[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-alkylation/oxidative 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. [ABSTRACT FROM AUTHOR]