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Media type:
E-Article
Title:
Continuous multistep synthesis of 2-(azidomethyl)oxazoles
Contributor:
Rossa, Thaís A;
Suveges, Nícolas S;
Sá, Marcus M;
Cantillo, David;
Kappe, C Oliver
Published:
Beilstein Institut, 2018
Published in:
Beilstein Journal of Organic Chemistry, 14 (2018), Seite 506-514
Language:
English
DOI:
10.3762/bjoc.14.36
ISSN:
1860-5397
Origination:
Footnote:
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 NaN3in 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.