Hydrazides in

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, ...

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. T ...

s with the formula RNHNH₂ where R is acyl (R'CO-), sulfonyl (R'SO₂-), or phosphoryl (R'₂P(O)-). Unlike 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 ''p''-Toluenesulfonyl hydrazide is the organic compound with the formula CH3C6H4SO2NHNH2. It is a white solid that is soluble in many organic solvents but not water or alkanes. It is a reagent in organic synthesis. Reactions With ketones and a ...

, 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 disc ...

and the

Eschenmoser–Tanabe fragmentation The Eschenmoser fragmentation, first published in 1967, is the chemical reaction of α,β-epoxy ketones (1) with aryl sulfonylhydrazines (2) to give alkynes (3) and carbonyl compounds (4). The reaction is named after the Swiss chemist Albert Eschen ...

. 2,4,6-Triisopropylbenzenesulfonylhydrazide is a useful source of

diimide Diimide, also called diazene or diimine, is a compound having the formula (NH)2. It exists as two geometric isomers, ''E'' (''trans'') and ''Z'' (''cis''). The term diazene is more common for organic derivatives of diimide. Thus, azobenzene is ...

Acyl hydrazide

Acylhydrazines are

derivatives The derivative of a function is the rate of change of the function's output relative to its input value. Derivative may also refer to: In mathematics and economics * Brzozowski derivative in the theory of formal languages * Formal derivative, an ...

of carboxylic acids, although they are typically prepared by the reaction of esters with hydrazine:

Use

An applied example is a synthesis of sunitinib begins by mixing 5-fluoro

isatin Isatin, also known as tribulin, is an organic compound derived from indole with formula C8H5NO2. The compound was first obtained by Otto Linné Erdman and Auguste Laurent in 1840 as a product from the oxidation of indigo dye by nitric acid and ...

slowly into

hydrazine hydrate 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 h ...

. 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 organic chemistry annulation (from the Latin ''anellus'' for "little ring"; occasionally annelation) is a chemical reaction in which a new ring is constructed on a molecule. : Examples are the Robinson annulation, Danheiser annulation and ce ...

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.

References

{{Hydrazines Functional groups

Sulfonyl hydrazides

Acyl hydrazide

Use

Uses

See also

References