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The Pellizzari reaction was discovered in 1911 by Guido Pellizzari, and is the organic reaction of an amide and a hydrazide to form a 1,2,4-triazole. [1] The product is similar to that of the Einhorn-Brunner reaction, but the mechanism itself is not regioselective. An overview of the Pellizzari reaction
An applied example is a synthesis of sunitinib begins by mixing 5-fluoroisatin slowly into hydrazine hydrate. [9] After 4 hours at 110 °C, the indole ring structure has been broken into (2-amino-5-fluoro-phenyl)-acetic acid hydrazide with reduction of the ketone at the 3-position.
[3] [4] An example of a transition metal-catalyzed cyclopropanation is a synthesis of tranylcypromine, [5] [6] in which the sodium salt of benzaldehyde tosylhydrazone is converted to a rhodium metal carbene through the diazo intermediate. Tosylhydrazones are also starting materials for certain cross-coupling reactions. [7]
Hydrazines (R 2 N−NR 2) are a class of chemical compounds with two nitrogen atoms linked via a covalent bond and which carry from one up to four alkyl or aryl substituents. . Hydrazines can be considered as derivatives of the inorganic hydrazine (H 2 N−NH 2), in which one or more hydrogen atoms have been replaced by hydrocarbon grou
The Shapiro reaction or tosylhydrazone decomposition is an organic reaction in which a ketone or aldehyde is converted to an alkene through an intermediate hydrazone in the presence of 2 equivalents of organolithium reagent.
Pigment Yellow 97, a popular yellow colorant, is a hydrazone. [6]Hydrazones are the basis for various analyses of ketones and aldehydes. For example, dinitrophenylhydrazine coated onto a silica sorbent is the basis of an adsorption cartridge.
The Wharton olefin synthesis or the Wharton reaction is a chemical reaction that involves the reduction of α,β-epoxy ketones using hydrazine to give allylic alcohols. [1] [2] [3] This reaction, introduced in 1961 by P. S. Wharton, is an extension of the Wolff–Kishner reduction.
In one variation called the Darapsky degradation, [19] or Darapsky synthesis, a Curtius rearrangement takes place as one of the steps in the conversion of an α-cyanoester to an amino acid. Hydrazine is used to convert the ester to an acylhydrazine , which is reacted with nitrous acid to give the acyl azide.