Oxidation of o-methoxyphenols with a hypervalent iodine reagent: Improved synthesis of asatone and demethoxyasatone

László Kürti, László Szilágyi, Sándor Antus, Mihály Nógrádi

Research output: Contribution to journalArticle

19 Citations (Scopus)

Abstract

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.

Original languageEnglish (US)
Pages (from-to)2579-2581
Number of pages3
JournalEuropean Journal of Organic Chemistry
Issue number10
StatePublished - Oct 1999

Fingerprint

Guaiacol
Phenol
Iodine
phenols
iodine
reagents
Methanol
methyl alcohol
analogs
Derivatives
Oxidation
oxidation
synthesis
products
phenyliodonium

Keywords

  • Asatone
  • Cyclohexa-2,4- dienones
  • Dimerization
  • Hypervalent iodine
  • Oxidation
  • Phenols

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Oxidation of o-methoxyphenols with a hypervalent iodine reagent : Improved synthesis of asatone and demethoxyasatone. / Kürti, László; Szilágyi, László; Antus, Sándor; Nógrádi, Mihály.

In: European Journal of Organic Chemistry, No. 10, 10.1999, p. 2579-2581.

Research output: Contribution to journalArticle

Kürti, László ; Szilágyi, László ; Antus, Sándor ; Nógrádi, Mihály. / Oxidation of o-methoxyphenols with a hypervalent iodine reagent : Improved synthesis of asatone and demethoxyasatone. In: European Journal of Organic Chemistry. 1999 ; No. 10. pp. 2579-2581.
@article{d5a9a070e6d54c388a81a31ee41004e9,
title = "Oxidation of o-methoxyphenols with a hypervalent iodine reagent: Improved synthesis of asatone and demethoxyasatone",
abstract = "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.",
keywords = "Asatone, Cyclohexa-2,4- dienones, Dimerization, Hypervalent iodine, Oxidation, Phenols",
author = "L{\'a}szl{\'o} K{\"u}rti and L{\'a}szl{\'o} Szil{\'a}gyi and S{\'a}ndor Antus and Mih{\'a}ly N{\'o}gr{\'a}di",
year = "1999",
month = "10",
language = "English (US)",
pages = "2579--2581",
journal = "Annalen der Pharmacie",
issn = "0075-4617",
publisher = "Wiley-VCH Verlag",
number = "10",

}

TY - JOUR

T1 - Oxidation of o-methoxyphenols with a hypervalent iodine reagent

T2 - Improved synthesis of asatone and demethoxyasatone

AU - Kürti, László

AU - Szilágyi, László

AU - Antus, Sándor

AU - Nógrádi, Mihály

PY - 1999/10

Y1 - 1999/10

N2 - 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.

AB - 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.

KW - Asatone

KW - Cyclohexa-2,4- dienones

KW - Dimerization

KW - Hypervalent iodine

KW - Oxidation

KW - Phenols

UR - http://www.scopus.com/inward/record.url?scp=0345425100&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0345425100&partnerID=8YFLogxK

M3 - Article

AN - SCOPUS:0345425100

SP - 2579

EP - 2581

JO - Annalen der Pharmacie

JF - Annalen der Pharmacie

SN - 0075-4617

IS - 10

ER -