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Curtius Rearrangements in which the isocyanate intermediate is reacted with benzyl alcohol provides the Cbz-Protected product. [412 mg, 66%] The acyl azide is usually made from the reaction of acid chlorides or anydrides with sodium azide or trimethylsilyl azide. An extension of the methodology using chloro- formate reagent and a catalytic amount of sodium tert- butoxide leads to the formation of a wide range of protect- ed anilines. To control N2 evolution, large-scale reactions are typically run with dose-controlled addition of DPPA at a moderate temperature. The Curtius rearrangement using DPPA Hofmann, Curtius, Schmidt, and Lossen rearrange- ments are well-known as a useful method to convert carboxylic acids or derivatives to amines or derivatives having one less carbon unit, whose key step is the transfer of a … Acyl azides are also obtained from treating acylhydrazines with nitrous acid. Curtius rearrangement Also known as: Curtius degradation The Curtius rearrangement is an organic reaction used to convert an acyl azide to an isocyanate under thermal conditions. The Curtius rearrangement of tetrazoles and related heterocyclic ring systems has long been recognized as a potential route to carbodiimides, and a number of highly reactive and unstable carbodiimides have been identified as intermediates in these pathways <2001EJOC2209, 2002JOC8538>. In one variation called the Darapsky degradation, or Darapsky synthesis, a Curtius rearrangement takes place as one of the steps in the conversion of an α-cyanoester to an amino acid. The mechanism consists of an alkyl shift of the R group from the carbonyl carbon to … DPPA (642 mg, 2.34 mmol) and TEA (236 mg, 2.34 mmol) were added to a solution of the SM (300 mg, 2.34 mmol) in t -BuOH (10 mL) at 50 C. The reaction mixture was stirred at 90 C for 16 h. After concentration, the residue was purified by silica gel column chromatography (1:4 PE / EtOAc) to provide the product as a yellow solid. Alternatively, the acyl azide can be formed by the direct reaction of a carboxylic acid with diphenylphosphoryl azide (DPPA). The Curtius Rearrangement is the thermal decomposition of carboxylic azides to produce an isocyanate. The new zinc-catalyzed Curtius rearrangement gives access to aliphatic Boc-protected amines at low tem- perature. The reaction sequence - including subsequent reaction with water which leads to amines - is named the Curtius Reaction. Hydrazine is used to convert the ester to an acylhydrazine, which is reacted with nitrous acid to give the acyl azide. These intermediates may be isolated, or their corresponding reaction or hydrolysis products may be obtained. the Curtius rearrangement hasbeen used in avariety of appli- cations.For example, akey Curtius rearrangement is involved for the establishment of the two neighboring nitrogen func- tionalities of Tamiflu (9), apotent and selective inhibitor of

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