A Two-Step Continuous-Flow Synthesis of N-(2-Aminoethyl)acylamides through Ring-Opening/Hydrogenation of Oxazolines

Harnessing hydrazoic acid in flow! 2‐Oxazolines can be ring‐opened in a very efficient manner by treatment with in situ generated hydrazoic acid. Despite the toxic and explosive nature of hydrazoic acid, this process can be conducted safely in a continuous‐flow format with residence times as short a...

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Bibliographic Details
Published in:Chemistry : a European journal 2011-11, Vol.17 (47), p.13146-13150
Main Authors: Gutmann, Bernhard, Roduit, Jean-Paul, Roberge, Dominique, Kappe, C. Oliver
Format: Article
Language:English
Subjects:
Chemistry
Explosions
Explosive forming
Format
Hydrazoic acid
Hydrogenation
microreactors
oxygen heterocycles
Synthesis
synthetic methods
Toxic
Toxicology
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Summary:Harnessing hydrazoic acid in flow! 2‐Oxazolines can be ring‐opened in a very efficient manner by treatment with in situ generated hydrazoic acid. Despite the toxic and explosive nature of hydrazoic acid, this process can be conducted safely in a continuous‐flow format with residence times as short as 5 min at 130 °C (see scheme).
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201102772