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Rhodium(III)-Catalyzed Intramolecular Annulation and Aromatization for the Synthesis of Pyrrolo[1,2-a]quinolines.

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A rhodium(III)-catalyzed protocol for the synthesis of pyrrolo[1,2-a]quinolines through intramolecular annulation of o-alkynyl amino aromatic ketones and subsequent aromatization is reported. This transformation builds the pyrrole and quinoline moieties of… Click to show full abstract

A rhodium(III)-catalyzed protocol for the synthesis of pyrrolo[1,2-a]quinolines through intramolecular annulation of o-alkynyl amino aromatic ketones and subsequent aromatization is reported. This transformation builds the pyrrole and quinoline moieties of the pyrrolo[1,2-a]quinoline in one pot and achieves a flexible introduction of different substituent groups at 4- and 5-positions on products that were difficult to prepare by other means. The reaction proceeds smoothly on a gram scale, and the products are amenable to downstream synthetic manipulations.

Keywords: intramolecular annulation; pyrrolo quinolines; rhodium iii; synthesis pyrrolo; iii catalyzed

Journal Title: Organic letters
Year Published: 2023

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