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A Straightforward Synthesis of Functionalized cis-Perhydroisoquinolin-1-ones

Laboratory of Organic Chemistry, Faculty of Pharmacy and Food Sciences, and Institute of Biomedicine (IBUB), University of Barcelona, 08028 Barcelona, Spain
Department of Nutrition, Food Sciences and Gastronomy, Faculty of Pharmacy and Food Sciences, and Institute of Nutrition and Food Safety (INSA-UB), University of Barcelona, 08921 Santa Coloma de Gramanet, Spain
Institut de Ciència de Materials de Barcelona (ICMAB-CSIC), Campus UAB, 08193 Cerdanyola, Spain
Author to whom correspondence should be addressed.
Academic Editors: David Díez and María Ángeles Castro
Molecules 2019, 24(3), 557;
Received: 15 January 2019 / Revised: 29 January 2019 / Accepted: 30 January 2019 / Published: 3 February 2019
(This article belongs to the Special Issue Application of Organic Synthesis to Bioactive Compounds)
PDF [2435 KB, uploaded 3 February 2019]


Base-catalyzed annulation reactions of 5,6-dihydro-2(1H)-pyridones with Nazarov-type reagents are reported. The effect of the solvent polarity and the concentration of the reagents is studied. The process involves two successive Michael additions and stereoselectively provides functionalized cis-perhydroisoquinolin-1-ones. View Full-Text
Keywords: 5,6-dihydro-2(1H)-pyridone; Nazarov reagents; perhydroisoquinoline; Michael addition; stereoselectivity 5,6-dihydro-2(1H)-pyridone; Nazarov reagents; perhydroisoquinoline; Michael addition; stereoselectivity

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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Arioli, F.; Pérez, M.; Are, C.; Molins, E.; Bosch, J.; Amat, M. A Straightforward Synthesis of Functionalized cis-Perhydroisoquinolin-1-ones. Molecules 2019, 24, 557.

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