- Source: Hydrazide
Hydrazides in organic chemistry are a class of organic compounds with the formula R−NR1−NR2R3 where R is acyl (R'−C(=O)−), sulfonyl (R'−S(=O)2−), phosphoryl ((R'−)2P(=O)−), phosphonyl ((R'−O−)2P(=O)−) and similar groups (chalcogen analogs are included, for example sulfur analogs called thiohydrazides), R1, R2, R3 and R' are any groups (typically hydrogen or organyl). 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, 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 and the Eschenmoser–Tanabe fragmentation.
2,4,6-Triisopropylbenzenesulfonylhydrazide is a useful source of diimide.
Acyl hydrazides
Acylhydrazines are derivatives 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-fluoroisatin 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.
See also
hydrazide imide - tautomeric form of amidrazone
References
Kata Kunci Pencarian:
- Luminol
- Hydrazide
- Phenylpiracetam hydrazide
- Luminol
- Maleic hydrazide
- Biotin hydrazide
- INH
- P-Toluenesulfonyl hydrazide
- Hydrochlorothiazide
- Amidrazone
- Isoniazid
