Facile one-pot preparation of 5-aryltetrazoles and 3-arylisoxazoles from aryl bromides

The successive treatment of aryl bromides with n-BuLi, DMF, hydroxylamine hydrochloride, and finally diphenylphosphoryl azide provided efficiently the corresponding 5-aryltetrazoles in good to moderate yields. Similarly, the successive treatment of aryl bromides with n-BuLi, DMF, hydroxylamine hydro...

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Bibliographic Details
Published inTetrahedron Vol. 74; no. 31; pp. 4226 - 4235
Main Authors Kobayashi, Eiji, Togo, Hideo
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 02.08.2018
Elsevier
Subjects
3-Arylisoxazole
5-Aryltetrazole
Aryl bromide
Chemistry
Chemistry, Organic
One-pot
Physical Sciences
Science & Technology
One-pot
5-Aryltetrazole
3-Arylisoxazole
Aryl bromide
5-SUBSTITUTED 1H-TETRAZOLES
EXCHANGE-REACTION
TETRAZOLES
CATALYZED SYNTHESIS
AZIDE
ISOXAZOLES
NITRILE OXIDES
1,3-DIPOLAR CYCLOADDITION
GENERATION
ALDOXIMES
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Summary:The successive treatment of aryl bromides with n-BuLi, DMF, hydroxylamine hydrochloride, and finally diphenylphosphoryl azide provided efficiently the corresponding 5-aryltetrazoles in good to moderate yields. Similarly, the successive treatment of aryl bromides with n-BuLi, DMF, hydroxylamine hydrochloride, and finally diethyl acetylenedicarboxylate and Oxone® provided efficiently the corresponding diethyl 3-arylisoxazole-4,5-dicarboxylates in good to moderate yields. Aromatic aldoximes are the key intermediates in both reactions, and 5-aryltetrazoles and 3-arylisoxazoles could be obtained from aryl bromides in one pot under transition-metal-free conditions. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2018.06.044