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

[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 b...

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Detalles Bibliográficos
Autores principales: Shimizu, Hisato, Yoshimura, Akira, Noguchi, Keiichi, Nemykin, Victor N, Zhdankin, Viktor V, Saito, Akio
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2018
Materias:
Letter
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5852453/
https://www.ncbi.nlm.nih.gov/pubmed/29623114
http://dx.doi.org/10.3762/bjoc.14.39
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author Shimizu, Hisato
Yoshimura, Akira
Noguchi, Keiichi
Nemykin, Victor N
Zhdankin, Viktor V
Saito, Akio
author_facet Shimizu, Hisato
Yoshimura, Akira
Noguchi, Keiichi
Nemykin, Victor N
Zhdankin, Viktor V
Saito, Akio
author_sort Shimizu, Hisato
collection PubMed
description [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.
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spelling pubmed-58524532018-04-05 Oxidative cycloaddition of hydroxamic acids with dienes or guaiacols mediated by iodine(III) reagents Shimizu, Hisato Yoshimura, Akira Noguchi, Keiichi Nemykin, Victor N Zhdankin, Viktor V Saito, Akio Beilstein J Org Chem Letter [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. Beilstein-Institut 2018-02-28 /pmc/articles/PMC5852453/ /pubmed/29623114 http://dx.doi.org/10.3762/bjoc.14.39 Text en Copyright © 2018, Shimizu et al. https://creativecommons.org/licenses/by/4.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Letter
Shimizu, Hisato
Yoshimura, Akira
Noguchi, Keiichi
Nemykin, Victor N
Zhdankin, Viktor V
Saito, Akio
Oxidative cycloaddition of hydroxamic acids with dienes or guaiacols mediated by iodine(III) reagents
title Oxidative cycloaddition of hydroxamic acids with dienes or guaiacols mediated by iodine(III) reagents
title_full Oxidative cycloaddition of hydroxamic acids with dienes or guaiacols mediated by iodine(III) reagents
title_fullStr Oxidative cycloaddition of hydroxamic acids with dienes or guaiacols mediated by iodine(III) reagents
title_full_unstemmed Oxidative cycloaddition of hydroxamic acids with dienes or guaiacols mediated by iodine(III) reagents
title_short Oxidative cycloaddition of hydroxamic acids with dienes or guaiacols mediated by iodine(III) reagents
title_sort oxidative cycloaddition of hydroxamic acids with dienes or guaiacols mediated by iodine(iii) reagents
topic Letter
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5852453/
https://www.ncbi.nlm.nih.gov/pubmed/29623114
http://dx.doi.org/10.3762/bjoc.14.39
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