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Break‐and‐Build Strategy for the Synthesis of 2‐Benzoylbenzoxazoles from o ‐Aminophenols and Acetophenones
Author(s) -
Nguyen Le Anh,
Ngo Quoc Anh,
Retailleau Pascal,
Nguyen Thanh Binh
Publication year - 2021
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.202100150
Subject(s) - chemistry , substrate (aquarium) , combinatorial chemistry , sulfur , scope (computer science) , functional group , reaction conditions , catalysis , organic chemistry , stereochemistry , oceanography , computer science , programming language , geology , polymer
Although compounds with a 2‐benzoylbenzoxazole motif are biologically relevant, there are only a few methods for synthesizing them, most of which relied on multistep process or required substrates bearing activating groups. Herein, we report an efficient method for the synthesis of such compounds by direct reactions of o ‐aminophenols with acetophenones promoted by sulfur in DMSO. The reaction was found to proceed via a Willgerodt rearrangement‐type benzoxazolation of acetophenones followed by a benzylic oxidation to reinstall the carbonyl function. This method has a broad substrate scope and good tolerance for sensitive functional groups.