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 (one less hydrogen at the point of attachment). Acylhydrazines are a type of hydrazides.
Carboxylic hydrazides are stable, polar solids and partially pharmacologically active.
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.
- Siegfried Hauptmann: Organische Chemie, 2. Auflage, VEB Deutscher Verlag für Grundstoffindustrie, Leipzig, 1985, S. 425, ISBN 3-342-00280-8.
- Siegfried Hauptmann: Organische Chemie, 2. Auflage, VEB Deutscher Verlag für Grundstoffindustrie, Leipzig, 1985, S. 426, ISBN 3-342-00280-8.
- "US patent 6573293".
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