Acylhydrazine
Acylhydrazines are a class of organic compounds and can be regarded as nitrogen derivatives of carboxylic acids having the general structure R-CO-NR1-NR2R3, where R1, R2 and R3 can be organic radicals or hydrogen. They are analogous to an amide, but the -OH portion of a carboxylic acid is replaced by hydrazine rather than ammonia. Acylhydrazines are a type of hydrazides.Preparation
Carboxylic hydrazides can be prepared by reacting acyl halides with hydrazine or by reduction of N-nitroso carboxamides.Properties
Carboxylic hydrazides are stable, polar solids and partially pharmacologically active.Use
Acylhydrazines are intermediates in chemical syntheses, for example in the synthesis of nitrogen heterocycles and acyl azides.
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 -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.
