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

László Kürti; László Szilágyi; Sándor Antus; Mihály Nógrádi

doi:10.1002/(sici)1099-0690(199910)1999:10<2579::aid-ejoc2579>3.0.co;2-h

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

László Kürti, László Szilágyi, Sándor Antus, Mihály Nógrádi

Biochemistry

Research output: Contribution to journal › Article › peer-review

20 Scopus citations

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 language	English (US)
Pages (from-to)	2579-2581
Number of pages	3
Journal	European Journal of Organic Chemistry
Issue number	10
DOIs	https://doi.org/10.1002/(sici)1099-0690(199910)1999:10<2579::aid-ejoc2579>3.0.co;2-h
State	Published - Oct 1999

Keywords

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

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1002/(sici)1099-0690(199910)1999:10<2579::aid-ejoc2579>3.0.co;2-h

Cite this

@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 = oct,

doi = "10.1002/(sici)1099-0690(199910)1999:10<2579::aid-ejoc2579>3.0.co;2-h",

language = "English (US)",

pages = "2579--2581",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

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

U2 - 10.1002/(sici)1099-0690(199910)1999:10<2579::aid-ejoc2579>3.0.co;2-h

DO - 10.1002/(sici)1099-0690(199910)1999:10<2579::aid-ejoc2579>3.0.co;2-h

M3 - Article

AN - SCOPUS:0345425100

SN - 1434-193X

SP - 2579

EP - 2581

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 10

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this