Premium
Selective synthesis of 2‐(5‐oxo‐1‐arylhex‐1‐yn‐3‐yl)phenyl benzoates via FeCl 3 ‐mediated cascade reactions of propargylamines with β ‐enamino ketones
Author(s) -
Tang Qiang,
He Xinwei,
Zhang Jinxue,
Zhou Tongtong,
Xie Mengqing,
Li Ruxue,
Zuo Youpeng,
Shang Yongjia
Publication year - 2020
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.5676
Subject(s) - chemistry , benzoates , intramolecular force , cascade , nucleophile , conjugate , hydrolysis , cascade reaction , medicinal chemistry , combinatorial chemistry , organic chemistry , catalysis , mathematical analysis , mathematics , chromatography
A mild and efficient FeCl 3 ‐mediated cascade reaction of ortho ‐hydroxyl propargylamines with β‐enamino ketones has been developed. This protocol provided a practical and selective method to synthesize 2‐(5‐oxo‐1‐arylhex‐1‐yn‐3‐yl)phenyl benzoates via in situ generated alkynyl o ‐quinone methides following a cascade intermolecular 1,4‐conjugate addition/intramolecular nucleophilic addition/reverse Claisen condensation/hydrolysis pathway. Furthermore, a series of 2‐(3‐oxo‐1‐arylbutyl)phenyl benzoates with good functional group tolerance were prepared in good to high yields under these reaction conditions.