We present a method for the synthesis of substituted indolo[1,2-a]quinoline-5(6H)-ones starting from 1-(2-ethynylphenyl)-1H-indoles. The transformation involves gold-catalyzed oxidation of the triple bond followed by acid-promoted intramolecular cyclization at the indole C2 position. Demonstrating noteworthy versatility, the reaction tolerates a wide array of substituents on the indole core and proceeds in good to excellent yields (up to 93%).
One‐Pot Gold/Acid‐Catalyzed Synthesis of Indolo[1,2‐a]quinolin‐5(6H)‐ones from 1‐(2‐Ethynylphenyl)‐1H‐indoles / E. Brambilla, M. Gugiatti, S. Rizzato, G. Abbiati, V. Pirovano. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - (2024), pp. e202400083.1-e202400083.9. [Epub ahead of print] [10.1002/ejoc.202400083]
One‐Pot Gold/Acid‐Catalyzed Synthesis of Indolo[1,2‐a]quinolin‐5(6H)‐ones from 1‐(2‐Ethynylphenyl)‐1H‐indoles
E. BrambillaPrimo
;S. Rizzato;G. AbbiatiPenultimo
;V. Pirovano
Ultimo
2024
Abstract
We present a method for the synthesis of substituted indolo[1,2-a]quinoline-5(6H)-ones starting from 1-(2-ethynylphenyl)-1H-indoles. The transformation involves gold-catalyzed oxidation of the triple bond followed by acid-promoted intramolecular cyclization at the indole C2 position. Demonstrating noteworthy versatility, the reaction tolerates a wide array of substituents on the indole core and proceeds in good to excellent yields (up to 93%).
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Eur J Org Chem - 2024 - Brambilla - One‐Pot Gold Acid‐Catalyzed Synthesis of Indolo 1 2‐a quinolin‐5 6H ‐ones from 1‐.pdf
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