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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.

SUBMITTER: Shimizu H

PROVIDER: S-EPMC5852453 | biostudies-literature | 2018

REPOSITORIES: biostudies-literature

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

Shimizu Hisato H Yoshimura Akira A Noguchi Keiichi K Nemykin Victor N VN Zhdankin Viktor V VV Saito Akio A

Beilstein journal of organic chemistry 20180228

[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 <i>o</i>-benzoquinones generated by the oxidative dearomatization of guaiacols. ...[more]

PMID: 29623114

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