Oxidative cycloaddition of hydroxamic acids with dienes or guaiacols mediated by iodine(III) reagents

Hisato Shimizu; Akira Yoshimura; Keiichi Noguchi; Victor N. Nemykin; Viktor V. Zhdankin; Akio Saito

doi:10.3762/bjoc.14.39

Oxidative cycloaddition of hydroxamic acids with dienes or guaiacols mediated by iodine(III) reagents

Hisato Shimizu, Akira Yoshimura, Keiichi Noguchi, Victor N. Nemykin, Viktor V. Zhdankin, Akio Saito

Chemistry & Biochemistry

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

4 Scopus citations

Abstract

[Bis(trifluoroacetoxy)iodo]benzene (BTI) and (diacetoxyiodo)benzene (DIB) efficiently promote the formation of acylnitroso species from hydroxamic acids in the presence of various dienes to give the corresponding hetero-Diels-Alder (HDA) adducts in moderate to high yields. The present method could be applied to the HDA reactions of acylnitroso species with o-benzoquinones generated by the oxidative dearomatization of guaiacols.

Original language	English (US)
Pages (from-to)	531-536
Number of pages	6
Journal	Beilstein Journal of Organic Chemistry
Volume	14
DOIs	https://doi.org/10.3762/bjoc.14.39
State	Published - Feb 28 2018

Bibliographical note

Publisher Copyright:
© 2018 Shimizu et al.

Keywords

Acylnitroso
Benzoquinone
Cycloaddition
Dearomatization
Iodine(III)

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10.3762/bjoc.14.39

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title = "Oxidative cycloaddition of hydroxamic acids with dienes or guaiacols mediated by iodine(III) reagents",

abstract = "[Bis(trifluoroacetoxy)iodo]benzene (BTI) and (diacetoxyiodo)benzene (DIB) efficiently promote the formation of acylnitroso species from hydroxamic acids in the presence of various dienes to give the corresponding hetero-Diels-Alder (HDA) adducts in moderate to high yields. The present method could be applied to the HDA reactions of acylnitroso species with o-benzoquinones generated by the oxidative dearomatization of guaiacols.",

keywords = "Acylnitroso, Benzoquinone, Cycloaddition, Dearomatization, Iodine(III)",

author = "Hisato Shimizu and Akira Yoshimura and Keiichi Noguchi and Nemykin, {Victor N.} and Zhdankin, {Viktor V.} and Akio Saito",

note = "Publisher Copyright: {\textcopyright} 2018 Shimizu et al.",

year = "2018",

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doi = "10.3762/bjoc.14.39",

language = "English (US)",

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T1 - Oxidative cycloaddition of hydroxamic acids with dienes or guaiacols mediated by iodine(III) reagents

AU - Shimizu, Hisato

AU - Yoshimura, Akira

AU - Noguchi, Keiichi

AU - Nemykin, Victor N.

AU - Zhdankin, Viktor V.

AU - Saito, Akio

PY - 2018/2/28

Y1 - 2018/2/28

N2 - [Bis(trifluoroacetoxy)iodo]benzene (BTI) and (diacetoxyiodo)benzene (DIB) efficiently promote the formation of acylnitroso species from hydroxamic acids in the presence of various dienes to give the corresponding hetero-Diels-Alder (HDA) adducts in moderate to high yields. The present method could be applied to the HDA reactions of acylnitroso species with o-benzoquinones generated by the oxidative dearomatization of guaiacols.

AB - [Bis(trifluoroacetoxy)iodo]benzene (BTI) and (diacetoxyiodo)benzene (DIB) efficiently promote the formation of acylnitroso species from hydroxamic acids in the presence of various dienes to give the corresponding hetero-Diels-Alder (HDA) adducts in moderate to high yields. The present method could be applied to the HDA reactions of acylnitroso species with o-benzoquinones generated by the oxidative dearomatization of guaiacols.

KW - Acylnitroso

KW - Benzoquinone

KW - Cycloaddition

KW - Dearomatization

KW - Iodine(III)

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DO - 10.3762/bjoc.14.39

M3 - Article

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AN - SCOPUS:85043577318

SN - 1860-5397

VL - 14

SP - 531

EP - 536

JO - Beilstein Journal of Organic Chemistry

JF - Beilstein Journal of Organic Chemistry

ER -

Oxidative cycloaddition of hydroxamic acids with dienes or guaiacols mediated by iodine(III) reagents

Abstract

Bibliographical note

Keywords

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