An Efficient Synthesis of 2,3-Diaryl-2-azabicyclooctanones Via BiCl3- Catalysed Three-Component aza Diels-Alder Reaction

Luis   Astudillo   S.; Gabriel   A.   Vallejos; Nestor      Correa; Margarita   Gutierrez   C.; Walesca      de la Guarda; Vladimir   V.   Kouznetsov

doi:10.2174/157017808785982301

Abstract

The first three-component coupling reactions between various anilines (1), benzaldehydes (2), and cyclohexen- 2-one (3) were performed under mild conditions (acetonitrile, room temperature, 14 h) in the presence of 20 mol % BiCl3 to obtain new 2,3-diaryl-2-aza[2.2.2]octan-5-ones (4,5) with interesting acetylcholinesterase inhibitory properties.

Keywords: 2,3-Diaryl-2-azabicyclo[2.2.2]octan-5-one, catalysed three-component aza Diels-Alder reaction, acetylcholinesterase inhibitors

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Letters in Organic Chemistry

Title: An Efficient Synthesis of 2,3-Diaryl-2-azabicyclooctanones Via BiCl3- Catalysed Three-Component aza Diels-Alder Reaction

Volume: 5 Issue: 7

Author(s): Luis Astudillo S., Gabriel A. Vallejos, Nestor Correa, Margarita Gutierrez C., Walesca de la Guarda and Vladimir V. Kouznetsov

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Keywords: 2,3-Diaryl-2-azabicyclo[2.2.2]octan-5-one, catalysed three-component aza Diels-Alder reaction, acetylcholinesterase inhibitors

Abstract: The first three-component coupling reactions between various anilines (1), benzaldehydes (2), and cyclohexen- 2-one (3) were performed under mild conditions (acetonitrile, room temperature, 14 h) in the presence of 20 mol % BiCl3 to obtain new 2,3-diaryl-2-aza[2.2.2]octan-5-ones (4,5) with interesting acetylcholinesterase inhibitory properties.

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S. Astudillo Luis, Vallejos A. Gabriel, Correa Nestor, C. Gutierrez Margarita, de la Guarda Walesca and Kouznetsov V. Vladimir, An Efficient Synthesis of 2,3-Diaryl-2-azabicyclooctanones Via BiCl3- Catalysed Three-Component aza Diels-Alder Reaction, Letters in Organic Chemistry 2008; 5 (7) . https://dx.doi.org/10.2174/157017808785982301