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A Novel Approach to N ‐Tf 2‐Aryl‐2,3‐Dihydroquinolin‐ 4(1 H )‐ones via a Ligand‐Free Pd(II)‐Catalyzed Oxidative Aza‐Michael Cyclization
Author(s) -
Kim Young Min,
Yoo HyungSeok,
Son Seung Hwan,
Kim Ga Yeong,
Jang Hyu Jeong,
Kim Dong Hwan,
Kim Soo Dong,
Park Boyoung Y.,
Kim NamJung
Publication year - 2021
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202001425
Subject(s) - chemistry , aryl , ligand (biochemistry) , combinatorial chemistry , catalysis , stereochemistry , palladium , yield (engineering) , oxidative addition , organic chemistry , biochemistry , receptor , alkyl , materials science , metallurgy
2‐Aryl‐2,3‐dihydroquinolin‐4(1 H )‐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(1 H )‐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(1 H )‐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.