Journal of Heterocyclic Chemistry

, volume 25 , issue 2 , pages 511-515

Selenium dioxide oxidation of alkylcoumarins and related methyl-substituted heteroaromatics

Kiichi Ito ¹

Kaoru Nakajima ¹

Hide authors affiliations Show authors affiliations: 1 affiliation

Hokkaido Institute of Pharmaceutical Sciences, Katsuraoka‐chc, Otaru‐shi, Hokkaido 047–02, Japan |

Publication type: Journal Article

Publication date: 1988-03-01

Wiley

Journal of Heterocyclic Chemistry

scimago Q3

wos Q2

SJR: 0.362

CiteScore: 4.7

Impact factor: 2.4

ISSN: 0022152X, 19435193

DOI: 10.1002/jhet.5570250229

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Organic Chemistry

Abstract

By the use of selenium dioxide as the specific oxidizing agent in the coumarin series, the 4-ethyl, 4-propyl and 4-benzyl substituents of coumarin were converted into α-alcohols 2 and/or ketones 3, while 3-methyl- and 3-benzylcoumarins were converted into 3-acyl derivatives 7. The methyl substituent of the analogous thiocoumarin 5, chromones 10 or thiochromone 11 was also oxidized into the formyl functionality. Facile oxidative desulfurization into the ketone functionality, prior to methyl oxidation, was observed for the thione derivatives of 1a, 5, 6 and 10.

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Lyssenko Konstantin

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DSc in Chemistry, professor

898 publications, 15 186 citations, 2 reviews

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Lomonosov Moscow State University

National Research University Higher School of Economics

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DSc in Chemistry, professor

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Ural Federal University

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GOST |

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GOST Copy

Ito K., Nakajima K. Selenium dioxide oxidation of alkylcoumarins and related methyl-substituted heteroaromatics // Journal of Heterocyclic Chemistry. 1988. Vol. 25. No. 2. pp. 511-515.

GOST all authors (up to 50) Copy

Ito K., Nakajima K. Selenium dioxide oxidation of alkylcoumarins and related methyl-substituted heteroaromatics // Journal of Heterocyclic Chemistry. 1988. Vol. 25. No. 2. pp. 511-515.

RIS |

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RIS Copy

TY - JOUR

DO - 10.1002/jhet.5570250229

UR - https://doi.org/10.1002/jhet.5570250229

TI - Selenium dioxide oxidation of alkylcoumarins and related methyl-substituted heteroaromatics

T2 - Journal of Heterocyclic Chemistry

AU - Ito, Kiichi

AU - Nakajima, Kaoru

PY - 1988

DA - 1988/03/01

PB - Wiley

SP - 511-515

IS - 2

VL - 25

SN - 0022-152X

SN - 1943-5193

ER -

BibTex |

Cite this

BibTex (up to 50 authors) Copy

@article{1988_Ito,

author = {Kiichi Ito and Kaoru Nakajima},

title = {Selenium dioxide oxidation of alkylcoumarins and related methyl-substituted heteroaromatics},

journal = {Journal of Heterocyclic Chemistry},

year = {1988},

volume = {25},

publisher = {Wiley},

month = {mar},

url = {https://doi.org/10.1002/jhet.5570250229},

number = {2},

pages = {511--515},

doi = {10.1002/jhet.5570250229}

}

MLA

Cite this

MLA Copy

Ito, Kiichi, and Kaoru Nakajima. “Selenium dioxide oxidation of alkylcoumarins and related methyl-substituted heteroaromatics.” Journal of Heterocyclic Chemistry, vol. 25, no. 2, Mar. 1988, pp. 511-515. https://doi.org/10.1002/jhet.5570250229.

Publisher

Wiley

Journal

Journal of Heterocyclic Chemistry

scimago Q3

wos Q2

SJR

0.362

CiteScore

4.7

Impact factor

2.4

ISSN

0022152X (Print)

19435193 (Electronic)