TY - JOUR A1 - Rossa, Thaís A. A1 - Suveges, Nícolas S. A1 - Sá, Marcus M. A1 - Cantillo, David A1 - Kappe, C. Oliver T1 - Continuous multistep synthesis of 2-(azidomethyl)oxazoles JF - Beilstein Journal of Organic Chemistry PY - 2018/// VL - 14 SP - 506 EP - 514 SN - 1860-5397 DO - 10.3762/bjoc.14.36 PB - Beilstein-Institut JA - Beilstein J. Org. Chem. UR - https://doi.org/10.3762/bjoc.14.36 KW - azirines KW - continuous flow KW - heterocycles KW - oxazoles KW - process integration KW - vinyl azides N2 - 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 NaN3 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. ER -