Hydrazide

Short description: Class of chemical compounds

Hydrazides in organic chemistry are a class of organic compounds with the formula R–NR1
–NR2

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),[1] R1
, R2
, R3
and R' are any groups (typically hydrogen or organyl).[2] Unlike hydrazine and alkylhydrazines, hydrazides are nonbasic owing to the inductive influence of the acyl, sulfonyl, or phosphoryl substituent.

## Contents

* 1 Sulfonyl hydrazides
* 2 Acyl hydrazides
* 2.1 Use
* 3 See also
* 4 References

## 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[3] and the Eschenmoser–Tanabe fragmentation.[4][5]

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

## Acyl hydrazides

An example of an acylhydrazine. This compound has been called acetylhydrazide, acetohydrazide, or acetic acid hydrazide.[7]

Acylhydrazines are derivatives of carboxylic acids, although they are typically prepared by the reaction of esters with hydrazine:[8]

### 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

1. ↑ "Search". https://chem-space.com/search/bb/exact/NNC%28%3DS%29c1ccccc1/004388e764d06aa0359aa04977357ef0. (subscription required)
2. ↑ IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997). Online corrected version:  (2006-) "Hydrazides". doi:10.1351/goldbook.H02879
3. ↑ Shapiro, Robert H. (1976). "Alkenes from Tosylhydrazones". Org. React. 23 (3): 405–507. doi:10.1002/0471264180.or023.03. ISBN 0471264180.
4. ↑ Schreiber, J.; Felix, D.; Eschenmoser, A.; Winter, M.; Gautschi, F.; Schulte-Elte, K. H.; Sundt, E.; Ohloff, G. et al. (1967). "Die Synthese von Acetylen-carbonyl-Verbindungen durch Fragmentierung von α-β-Epoxy-ketonen mit p-Toluolsulfonylhydrazin. Vorläufige Mitteilung" (in German). Helv. Chim. Acta 50 (7): 2101–2108. doi:10.1002/hlca.19670500747.
5. ↑ 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.
6. ↑ 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.
7. ↑ "ChemicalBook:2-(4-ethylphenoxy)acetylhydrazide". http://www.chemicalbook.com/ChemicalProductProperty_EN.aspx?CBNumber=CB0727806. Retrieved 24 May 2023.
8. ↑ Schirmann, Jean-Pierre; Bourdauducq, Paul (2001). "Ullmann's Encyclopedia of Industrial Chemistry". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a13_177.
9. ↑ "US patent 6573293". http://www.patentlens.net/patentlens/structured.cgi?patnum=US_6573293#show.

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Hydrazines

* 4-PTSC
* Acylhydrazine
* ADH
* Adjudin
* Agaritine
* Benmoxin
* Cadralazine
* Carbazide
* Carbidopa
* Carbohydrazide
* Daminozide
* Dihydralazine
* DNPH
* Endralazine
* Gyromitrin
* HBT
* Hydralazine
* Hydrazide
* Hydrazine
* Hydrazone
* Iproclozide
* Iproniazid
* Isocarboxazid
* Isoniazid
* Mebanazine
* Metfendrazine
* MMH
* Nialamide
* Octamoxin
* PEH
* Phenelzine
* Pheniprazine
* Phenoxypropazine
* Phenylhydrazine
* Pildralazine
* Pimagedine
* Pivalylbenzhydrazine
* Procarbazine
* Safrazine
* Semicarbazide
* Semicarbazone
* SDMH
* Tetrafluorohydrazine
* UDMH

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