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Organic‐Inorganic Dual Catalytic System for the Regioselective Construction of Diverse Quinone Derivatives via Benzannulation
Author(s) -
Akhtar Muhammad Saeed,
Yang WonGuen,
Kim Sung Hong,
Lee Yong Rok
Publication year - 2021
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.202000725
Subject(s) - regioselectivity , chemistry , cycloaddition , anthracene , catalysis , quinone , naphthoquinone , organic chemistry , annulation , anthraquinone , adduct , combinatorial chemistry , medicinal chemistry
Efficient and regioselective synthesis of highly functionalized naphthoquinone and anthraquinone derivatives was accomplished in good yields using an organic‐inorganic dual catalyst through [4+2] cycloaddition reaction between various 1,4‐benzenediols or 1,4‐naphthalenediols and α , β ‐unsaturated aldehydes. These atom‐economic reactions rapidly provided useful cycloaddition adducts in a one‐pot reaction. The technique was successfully applied to synthesize tectoquinone, a natural compound found in red heartwood‐type Cryptomeria japonica , and 2‐(4‐methylpent‐3‐enyl)anthracene‐9,10‐dione, found in the roots of Sesamum indicum , and their analogs.