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Oxidation of o ‐Methoxyphenols with a Hypervalent Iodine Reagent: Improved Synthesis of Asatone and Demethoxyasatone
Author(s) -
Kürti László,
Szilágyi László,
Antus Sándor,
Nógrádi Mihály
Publication year - 1999
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/(sici)1099-0690(199910)1999:10<2579::aid-ejoc2579>3.0.co;2-h
Subject(s) - hypervalent molecule , chemistry , reagent , phenol , iodine , methanol , organic chemistry , combinatorial chemistry , medicinal chemistry
Oxidation of the 2‐methoxyphenols 1c–f with phenyliodonium(III) diacetate (PIDA) in methanol resulted in the formation of the cyclohexa‐2,4‐dienones 4c–f , which dimerized spontaneously to a single product ( 5c–f ) in each case. Using this method the synthesis of asatone ( 5a ) and its demethoxy analogue ( 5b ) was also accomplished starting from the readily available phenol derivatives 1a and 1b , respectively.