Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2021, Issue 4, Pages 618-622Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.202001425
Keywords
2-Aryl-2; 3-dihydroquinolin-4(1H)-one; Dehydrogenation; Michael addition; Palladium; Quinoline
Categories
Funding
- National Research Foundation of Korea (NRF) - Korea government (MSIT) [NRF - 2019R1H1A2079819, 2020R1F1A1064755]
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2-Aryl-2,3-dihydroquinolin-4(1H)-ones have been identified as important structures with potent biological activities. In this study, 25 novel N-Tf 2-aryl-2,3-dihydroquinolin-4(1H)-ones were efficiently synthesized via oxidative aza-Michael cyclization. This methodology offers advantages such as short reaction times and suitable functional group tolerance.
2-Aryl-2,3-dihydroquinolin-4(1H)-ones have recently been identified as important structures with potent biological activities such as antitumor and antidiabetic effect. Herein, a total of 25 novel N-Tf 2-aryl-2,3-dihydroquinolin-4(1H)-ones were expediently synthesized via the oxidative aza-Michael cyclization of N-Tf-2 '-aminodihydrochalcones by ligand-free palladium(II) catalysis. This study presents a new synthetic approach to yield N-Tf 2-aryl-2,3-dihydroquinolin-4(1H)-ones, which can be easily transformed into pharmacologically interesting aza-flavanones and other N-heterocycles, such as quinolines and tetrahydroquinolines, in yields up to 84 %. This methodology has various advantages, which includes short reaction times under mild conditions and suitable functional group tolerance. Furthermore, a plausible mechanism was proposed and demonstrated by kinetic analysis.
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