Hydrazide

Source: Wikipedia, the free encyclopedia.

Hydrazides in

organyl).[2] 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

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

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

Wikimedia Commons has media related to Hydrazides.
  1. ^ "Search". chem-space.com. Retrieved 24 May 2023. (subscription required)
  2. doi:10.1351/goldbook.H02879
  3. ISBN 0471264180
    .
  4. doi:10.1002/hlca.19670500747
    .
  5. doi:10.1016/S0040-4039(01)89757-4
    .
  6. ISBN 978-0471936237
    .
  7. ^ "ChemicalBook:2-(4-ethylphenoxy)acetylhydrazide". Retrieved 24 May 2023.
  8. ISBN 978-3527306732
    .
  9. ^ "US patent 6573293". Archived from the original on 2012-09-06.
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