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Piperonal, like all aldehydes, can be reduced to its alcohol (piperonyl alcohol) or oxidized to give its acid (piperonylic acid). Piperonal can be used in the synthesis of some pharmaceutical drugs including tadalafil, [7] L-DOPA, [8] and atrasentan. [9]
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.
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.
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can be considered as derivatives of the inorganic hydrazine (H 2 N−NH 2), in which one or more hydrogen atoms have been replaced by hydrocarbon grou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 Wolff–Kishner reduction is a reaction used in organic chemistry to convert carbonyl functionalities into methylene groups. [1] [2] In the context of complex molecule synthesis, it is most frequently employed to remove a carbonyl group after it has served its synthetic purpose of activating an intermediate in a preceding step.
A related hydrazide auxiliary is the chiral acryloylhydrazide, which reacts diastereoselectively with aldehydes. [22] Both diastereomers could be obtained with different choice of solvents (DMSO vs. mixed THF and H 2 O), suggesting that the transition structure conformation is solvent-influenced.
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.
[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]