Hydrazide
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Hydrazides in organic chemistry are a class of organic compounds with the formula Page Module:Chem2/styles.css has no content.R−NR1−NR2R3 where R is acyl (Page Module:Chem2/styles.css has no content.R'−C(=O)−), sulfonyl (Page Module:Chem2/styles.css has no content.R'−S(=O)2−), phosphoryl (Page Module:Chem2/styles.css has no content.(R'−)2P(=O)−), phosphonyl (Page Module:Chem2/styles.css has no content.(R'−O−)2P(=O)−), etc. and Page Module:Chem2/styles.css has no content.R1, R2, R3 and R' are any groups (typically hydrogen or organyl).[1] 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. 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 hydrazides
Acylhydrazines are derivatives of carboxylic acids, although they are typically prepared by the reaction of esters with hydrazine.[7]
Transamidation is possible but requires long-duration heat, and acyl moieties rarely migrate off another hydrazide.[8]Template:Rp An exception are the chloral hydrazones, which deacylate easily.[8]Template:Rp
Alternatively, bromine oxidizes aldehydic hydrazones to a hydrazidoyl bromide, which then hydrolyzes to an acyl hydrazide.[8]Template:Rp
Lithium aluminum hydride reduces acylhydrazides to the hydrazine only if the hydrazide lacks a labile proton.[8]Template:Rp
Use
An applied example is a synthesis of sunitinib begins by mixing 5-fluoroisatin slowly into hydrazine hydrate.[9] 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
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- ^ IUPAC, Compendium of Chemical Terminology, 5th ed. (the "Gold Book") (2025). Online version: (2006–) "Hydrazides". Script error: No such module "CS1 identifiers".
- ^ Page Module:Citation/CS1/styles.css has no content.Shapiro, Robert H. (1976). "Alkenes from Tosylhydrazones". Org. React. 23 (3): 405–507. doi:10.1002/0471264180.or023.03. ISBN 0471264180.
- ^ Page Module:Citation/CS1/styles.css has no content.Schreiber, J.; Felix, D.; Eschenmoser, A.; Winter, M.; Gautschi, F.; Schulte-Elte, K. H.; Sundt, E.; Ohloff, G.; Kalovoda, J.; Kaufmann, H.; Wieland, P.; Anner, G. (1967). "Die Synthese von Acetylen-carbonyl-Verbindungen durch Fragmentierung von α,β-Epoxy-ketonen mit p-Toluolsulfonylhydrazin. Vorläufige Mitteilung". Helv. Chim. Acta (in German). 50 (7): 2101–2108. doi:10.1002/hlca.19670500747.
{{cite journal}}: CS1 maint: unrecognized language (link) - ^ Page Module:Citation/CS1/styles.css has no content.Tanabe, Masato; Crowe, David F.; Dehn, Robert L. (1967). "A novel fragmentation reaction of α,β-epoxyketones the synthesis of acetylenic ketones". Tetrahedron Lett. 8 (40): 3943–3946. doi:10.1016/S0040-4039(01)89757-4.
- ^ Page Module:Citation/CS1/styles.css has no content.Chamberlin, A. Richard; Sheppeck, James E.; Somoza, Alvaro (2008). "2,4,6-Triisopropylbenzenesulfonylhydrazide". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rt259.pub2. ISBN 978-0471936237.
- ^ Page Module:Citation/CS1/styles.css has no content."ChemicalBook:2-(4-ethylphenoxy)acetylhydrazide". Retrieved 24 May 2023.
- ^ Script error: No such module "Template wrapper".
- ^ a b c d Page Module:Citation/CS1/styles.css has no content.Paulsen, Hans; Stoye, Dieter (1970). "The chemistry of hydrazides". In Zabicky, Jacob (ed.). The Chemistry of Amides. The Chemistry of Functional Groups. London: Interscience (Wiley). pp. 515–600. doi:10.1002/9780470771235. ISBN 0-471-98049-8. LCCN 76-116520.
- ^ Page Module:Citation/CS1/styles.css has no content."US patent 6573293".
{{cite web}}: CS1 maint: deprecated archival service (link)
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