Hypervalent iodine-induced formation of 3,5-disubstituted isoxazoles via [3 + 2] cycloaddition of diynes with aldoximes

A direct and efficient synthetic route for [3 + 2] cycloaddition of diynes with aldoximes induced by hypervalent iodine has been described, thus providing 3,5-disubstituted isoxazoles in moderate to good yields with high regioselectivity at room temperature. This transformation was carried out in th...

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Published inMonatshefte für Chemie Vol. 148; no. 6; pp. 1109 - 1116
Main Authors Xu, Fen, Kang, Wei-Fen, Wang, Xiao-Ning, Zhu, Ying-Ying, Chen, San-Xu, Kong, Yue-Jie, Fang, Shao-Ming
Format Journal Article
LanguageEnglish
Published Vienna Springer Vienna 01.06.2017
Springer Nature
Springer Nature B.V
Subjects
Analytical Chemistry
Benzene
Chemistry
Chemistry and Materials Science
Chemistry, Multidisciplinary
Chemistry/Food Science
Cycloaddition
Inorganic Chemistry
Iodine
Organic Chemistry
Original Paper
Physical Chemistry
Physical Sciences
Regioselectivity
Room temperature
Science & Technology
Theoretical and Computational Chemistry
Isoxazoles
Oxides
Cycloadditions
Alkynes
OXIMES
ANALOGS
ARENES
GENERATION
NITRILE OXIDE CYCLOADDITIONS
INHIBITORS
CATALYST
DERIVATIVES
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Summary:A direct and efficient synthetic route for [3 + 2] cycloaddition of diynes with aldoximes induced by hypervalent iodine has been described, thus providing 3,5-disubstituted isoxazoles in moderate to good yields with high regioselectivity at room temperature. This transformation was carried out in the presence of [bis(trifluoroacetoxy)iodo]benzene as a promoter and demonstrated high levels of functional-group tolerance. Graphical abstract
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ISSN:0026-9247
1434-4475
DOI:10.1007/s00706-016-1907-3