4.4 Article

Azido-Schmidt reaction for the formation of amides, imides and lactams from ketones in the presence of FeCl3

Journal

TETRAHEDRON LETTERS
Volume 49, Issue 32, Pages 4742-4745

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2008.05.113

Keywords

Schmidt reaction; ketones; sodium azide; amides; imides and lactams

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Ketones undergo smooth rearrangement with TMSN3 in the presence of FeCl3 under extremely mild conditions to provide the corresponding amides, imides and lactams in good yields with high selectivity. This method is very useful for the preparation of a wide range of amides, imides and lactams from ketones. The use of FeCl3 makes this method simple, convenient and cost-effective. (C) 2008 Elsevier Ltd. All rights reserved.

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