A single-pot synthesis of 4-hydroxybenzophenones via acid-catalyzed alkoxylation of p -quinone methides followed by DDQ-assisted oxo-demethoxylation

A highly efficient protocol has been developed in this work to synthesize promising pharmacophore synthons, namely 4-hydroxybenzophenones (4-HBP), with yields ranging from 80–99%. Interestingly, the method utilizes p -QMs as substrates and involves a single-pot, two-step alkoxylation/oxo-demethoxyla...

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Bibliographic Details
Published in:New journal of chemistry 2023-10, Vol.47 (39), p.18419-18429
Main Authors: Mahey, Jasbir Kaur, Pawara, Chunilal B., Kamble, Sumit B.
Format: Article
Language:English
Subjects:
Chemical synthesis
Functional groups
Oxidation
Quinones
Recyclability
Regioselectivity
Room temperature
Substrates
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Summary:A highly efficient protocol has been developed in this work to synthesize promising pharmacophore synthons, namely 4-hydroxybenzophenones (4-HBP), with yields ranging from 80–99%. Interestingly, the method utilizes p -QMs as substrates and involves a single-pot, two-step alkoxylation/oxo-demethoxylation reaction sequence that uses easily accessible Amberlyst-15 and DDQ, respectively, in methanol at room temperature. The protocol demonstrates a broad substrate scope for diverse p -QMs with excellent functional group tolerance and complete regioselectivity for oxidation at the methide group. Moreover, the synthesized compounds 1 could be readily dealkylated to 4-HBPs (9), a key starting material of top-selling drugs. The simple starting materials, and the scalability (1 g) and recyclability of both Amberlyst-15 and DDQ over at least five cycles make the protocol eco-friendly and commercially viable.
ISSN:1144-0546
1369-9261
DOI:10.1039/D3NJ03163B