Chemical reaction between an azide and a carbonyl derivative
Schmidt reaction
Named after
Karl Friedrich Schmidt
Reaction type
Rearrangement reaction
Identifiers
Organic Chemistry Portal
schmidt-reaction
RSC ontology ID
RXNO:0000170
In organic chemistry, the Schmidt reaction is an organic reaction in which an azide reacts with a carbonyl derivative, usually an aldehyde, ketone, or carboxylic acid, under acidic conditions to give an amine or amide, with expulsion of nitrogen.[1][2][3] It is named after Karl Friedrich Schmidt (1887–1971), who first reported it in 1924 by successfully converting benzophenone and hydrazoic acid to benzanilide.[4] The intramolecular reaction was not reported until 1991[5] but has become important in the synthesis of natural products.[6]
The reaction is effective with carboxylic acids to give amines (above), and with ketones to give amides (below).
^Plagens, Andreas; Laue, Thomas M. (2005). Named organic reactions (2nd ed.). Chichester: John Wiley & Sons. ISBN 0-470-01041-X.
^Wolff, Hans (2011). "The Schmidt Reaction". Organic Reactions: 307–336. doi:10.1002/0471264180.or003.08. ISBN 978-0471264187.
^Lang, S.; Murphy, J. A. (2006). "Azide rearrangements in electron-deficient systems". Chem. Soc. Rev. 35 (2): 146–156. doi:10.1039/B505080D. PMID 16444296.
^Schmidt, K. F. (1924). "Über den Imin-Rest". Berichte der Deutschen Chemischen Gesellschaft (A and B Series). 57 (4): 704–723. doi:10.1002/cber.19240570423.
^Jeffrey Aube & Gregory L. Milligan (1991). "Intramolecular Schmidt reaction of alkyl azides". J. Am. Chem. Soc.113 (23): 8965–8966. doi:10.1021/ja00023a065.
^Nyfeler, Erich; Renaud, Philippe (24 May 2006). "Intramolecular Schmidt Reaction: Applications in Natural Product Synthesis". Chimia International Journal for Chemistry. 60 (5): 276–284. doi:10.2533/000942906777674714.
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