Hydrazides in organic chemistry are a class of organic compounds with the formula RNHNH₂ where R is acyl (R'CO-), sulfonyl (R'SO₂-), or phosphoryl (R'₂P(O)-).^[1] Unlike hydrazine and alkylhydrazines, hydrazides are nonbasic owing to the inductive influence of the acyl, sulfonyl, or phosphoryl substituent.

Sulfonyl hydrazides

Tosyl hydrazide

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^[2] and the Eschenmoser–Tanabe fragmentation.^[3][4]

2,4,6-Triisopropylbenzenesulfonylhydrazide is a useful source of diimide.^[5]

Acyl hydrazide

An example of an acylhydrazine. This compound has been called acetylhydrazide, acetohydrazide, or acetic acid hydrazide.^[6]

Acylhydrazines are derivatives of carboxylic acids, although they are typically prepared by the reaction of esters with hydrazine:^[7]

Use

An applied example is a synthesis of sunitinib begins by mixing 5-fluoroisatin slowly into hydrazine hydrate.^[8] 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 amidrazone

References

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