page_title: Schmidt reaction
section_title: Reactions involving alkyl azides
hierarchical_section_title: Schmidt reaction / Reactions involving alkyl azides
caption_attribution_description: Boyer reaction
context_page_description: The Schmidt reaction is an organic reaction in which an azide reacts with a carbonyl derivative, usually a aldehyde, ketone, or carboxylic acid, under acidic conditions to give an amine or amide, with expulsion of nitrogen. It is named after Karl Friedrich Schmidt, who first reported it in 1924 by successfully converting benzophenone and hydrazoic acid to benzanilide. Surprisingly, the intramolecular reaction was not reported until 1991 but has become important in the synthesis of natural products.
  The reaction is effective with carboxylic acids to give amines, and with ketones to give amides.
context_section_description: The scope of this reaction has been extended to reactions of carbonyls with alkyl azides R-N₃. This extension was first reported by J.H. Boyer in 1955  (hence the name Boyer reaction), for example, the reaction of m-nitrobenzaldehyde with β-azido-ethanol:
  Variations involving intramolecular Schmidt reactions have been known since 1991. These are annulation reactions and have some utility in the synthesis of natural products; such as lactams and alkaloids.
caption: The Boyer reaction
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