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    Continuous multistep synthesis of 2-(azidomethyl)oxazoles (2018)
    Beilstein-Institut
    Details
    Publication Date: 2018-03-06
    Description: An efficient three-step protocol was developed to produce 2-(azidomethyl)oxazoles from vinyl azides in a continuous-flow process. The general synthetic strategy involves a thermolysis of vinyl azides to generate azirines, which react with bromoacetyl bromide to provide 2-(bromomethyl)oxazoles. The latter compounds are versatile building blocks for nucleophilic displacement reactions as demonstrated by their subsequent treatment with NaN 3 in aqueous medium to give azido oxazoles in good selectivity. Process integration enabled the synthesis of this useful moiety in short overall residence times (7 to 9 min) and in good overall yields. Beilstein J. Org. Chem. 2018, 14, 506–514. doi:10.3762/bjoc.14.36
    Keywords: azirinescontinuous flowheterocyclesoxazolesprocess integrationvinyl azides
    Electronic ISSN: 1860-5397
    Topics: Chemistry and Pharmacology
    Published by Beilstein-Institut
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