Hypervalent Iodine(III) Reagent Mediated Regioselective Cycloaddition of Aldoximes with Enaminones

Akira Yoshimura, Melissa E. Jarvi, Michael T. Shea, Cody L. Makitalo, Gregory T. Rohde, Mekhman S. Yusubov, Akio Saito, Viktor V. Zhdankin

Исследовательская школа химических и биомедицинских технологий

Результат исследований: Материалы для журнала › Статья

1 Цитирования (Scopus)

Аннотация

An efficient oxidative cycloaddition of enaminones with nitrile oxides generated in situ from respective aldoximes using hypervalent iodine reagents has been developed. Reactions of various aldoximes with enaminones in the presence of [hydroxy(tosyloxy)iodo]benzene involved the regioselective cycloaddition reaction resulting in the formation of the 3,4-disubstituted isoxazoles in moderate to good yields. Structures of several isoxazole products were confirmed by a single X-ray crystallography.

Язык оригинала	Английский
Страницы (с-по)	6682-6689
Число страниц	8
Журнал	European Journal of Organic Chemistry
Том	2019
Номер выпуска	39
DOI	https://doi.org/10.1002/ejoc.201901258
Состояние	Опубликовано - 24 окт 2019

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry

Доступ к документу

10.1002/ejoc.201901258

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Цитировать

Yoshimura, A., Jarvi, M. E., Shea, M. T., Makitalo, C. L., Rohde, G. T., Yusubov, M. S., Saito, A., & Zhdankin, V. V. (2019). Hypervalent Iodine(III) Reagent Mediated Regioselective Cycloaddition of Aldoximes with Enaminones. European Journal of Organic Chemistry, 2019(39), 6682-6689. https://doi.org/10.1002/ejoc.201901258

Hypervalent Iodine(III) Reagent Mediated Regioselective Cycloaddition of Aldoximes with Enaminones. / Yoshimura, Akira; Jarvi, Melissa E.; Shea, Michael T.; Makitalo, Cody L.; Rohde, Gregory T.; Yusubov, Mekhman S.; Saito, Akio; Zhdankin, Viktor V.

В: European Journal of Organic Chemistry, Том 2019, № 39, 24.10.2019, стр. 6682-6689.

Результат исследований: Материалы для журнала › Статья

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title = "Hypervalent Iodine(III) Reagent Mediated Regioselective Cycloaddition of Aldoximes with Enaminones",

abstract = "An efficient oxidative cycloaddition of enaminones with nitrile oxides generated in situ from respective aldoximes using hypervalent iodine reagents has been developed. Reactions of various aldoximes with enaminones in the presence of [hydroxy(tosyloxy)iodo]benzene involved the regioselective cycloaddition reaction resulting in the formation of the 3,4-disubstituted isoxazoles in moderate to good yields. Structures of several isoxazole products were confirmed by a single X-ray crystallography.",

keywords = "Aldoximes, Cycloaddition, Hypervalent iodine(III) reagents, Isoxazoles, Regioselectivity",

author = "Akira Yoshimura and Jarvi, {Melissa E.} and Shea, {Michael T.} and Makitalo, {Cody L.} and Rohde, {Gregory T.} and Yusubov, {Mekhman S.} and Akio Saito and Zhdankin, {Viktor V.}",

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T1 - Hypervalent Iodine(III) Reagent Mediated Regioselective Cycloaddition of Aldoximes with Enaminones

AU - Yoshimura, Akira

AU - Jarvi, Melissa E.

AU - Shea, Michael T.

AU - Makitalo, Cody L.

AU - Rohde, Gregory T.

AU - Yusubov, Mekhman S.

AU - Saito, Akio

AU - Zhdankin, Viktor V.

PY - 2019/10/24

Y1 - 2019/10/24

N2 - An efficient oxidative cycloaddition of enaminones with nitrile oxides generated in situ from respective aldoximes using hypervalent iodine reagents has been developed. Reactions of various aldoximes with enaminones in the presence of [hydroxy(tosyloxy)iodo]benzene involved the regioselective cycloaddition reaction resulting in the formation of the 3,4-disubstituted isoxazoles in moderate to good yields. Structures of several isoxazole products were confirmed by a single X-ray crystallography.

AB - An efficient oxidative cycloaddition of enaminones with nitrile oxides generated in situ from respective aldoximes using hypervalent iodine reagents has been developed. Reactions of various aldoximes with enaminones in the presence of [hydroxy(tosyloxy)iodo]benzene involved the regioselective cycloaddition reaction resulting in the formation of the 3,4-disubstituted isoxazoles in moderate to good yields. Structures of several isoxazole products were confirmed by a single X-ray crystallography.

KW - Aldoximes

KW - Cycloaddition

KW - Hypervalent iodine(III) reagents

KW - Isoxazoles

KW - Regioselectivity

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