Hydrazide on:
[Wikipedia]
[Google]
[Amazon]
Hydrazides in
A common sulfonyl hydrazide is p-toluenesulfonyl hydrazide, a white air-stable solid. They are also widely used as organic reagents.
Toluenesulfonyl hydrazide is used to generate toluenesulfonyl hydrazones. When derived from ketones, these hydrazones participate in the
organic chemistry
Organic chemistry is a subdiscipline within chemistry involving the scientific study of the structure, properties, and reactions of organic compounds and organic materials, i.e., matter in its various forms that contain carbon atoms.Clayden, J ...
are a class of organic compound
In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. Th ...
s with the formula RNHNH2 where R is acyl (R'CO-), sulfonyl (R'SO2-), or phosphoryl (R'2P(O)-). Unlike hydrazine
Hydrazine is an inorganic compound with the chemical formula . It is a simple pnictogen hydride, and is a colourless flammable liquid with an ammonia-like odour. Hydrazine is highly toxic unless handled in solution as, for example, hydrazine ...
and alkylhydrazines, hydrazides are nonbasic owing to the inductive influence of the acyl, sulfonyl, or phosphoryl substituent.
Sulfonyl hydrazides
A common sulfonyl hydrazide is p-toluenesulfonyl hydrazide, a white air-stable solid. They are also widely used as organic reagents.
Toluenesulfonyl hydrazide is used to generate toluenesulfonyl hydrazones. When derived from ketones, these hydrazones participate in the Shapiro reaction
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. The reaction was discov ...
and the Eschenmoser–Tanabe fragmentation.
2,4,6-Triisopropylbenzenesulfonylhydrazide is a useful source of diimide.
Acyl hydrazide
Acylhydrazines are derivatives ofcarboxylic acid
In organic chemistry, a carboxylic acid is an organic acid that contains a carboxyl group () attached to an R-group. The general formula of a carboxylic acid is or , with R referring to the alkyl, alkenyl, aryl, or other group. Carboxyli ...
s, although they are typically prepared by the reaction of esters with hydrazine:
Use
An applied example is a synthesis ofsunitinib
Sunitinib, sold under the brand name Sutent, is a medication used to treat cancer. It is a small-molecule, multi-targeted receptor tyrosine kinase (RTK) inhibitor that was approved by the FDA for the treatment of renal cell carcinoma (RCC) and i ...
begins by mixing 5-fluoro isatin slowly into hydrazine hydrate. 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. Subsequent annelation in strong acid creates the 1,3-dihydro-2-oxo indole structure required for the drug.Uses
1.) Hydrazide analogs has biological activities like antidepressant, anticonvulsant, antiinflammatory, antibacterial, antimalarial, anticancer, and antimicrobial. 2.) Hydrazide is a drug used as a tablet. It is typically used for the treatment of edema, high blood pressure or hypertension.See also
* hydrazide imide - tautomeric form of amidrazoneReferences
{{Hydrazines Functional groups