Propargylamine is an
organic compound
Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...
with the formula HC≡CCH
2NH
2. It is a colorless, odorless liquid that is used as a precursor to other compounds. Propargyl amines are produced by reactions of amines with propargyl halides.
The behavior of propargyl amine is illustrated by its acylation
benzoyl chloride
Benzoyl chloride, also known as benzenecarbonyl chloride, is an organochlorine compound with the formula . It is a colourless, fuming liquid with an irritating odour, and consists of a benzene ring () with an acyl chloride () substituent. It is ...
to the
amide
In organic chemistry, an amide, also known as an organic amide or a carboxamide, is a chemical compound, compound with the general formula , where R, R', and R″ represent any group, typically organyl functional group, groups or hydrogen at ...
. A
Sonogashira coupling
The Sonogashira reaction is a cross-coupling reaction used in organic synthesis to form carbon–carbon bonds. It employs a palladium catalyst as well as copper co-catalyst to form a carbon–carbon bond between a terminal alkyne and an aryl or vi ...
of the terminal
alkyne
\ce
\ce
Acetylene
\ce
\ce
\ce
Propyne
\ce
\ce
\ce
\ce
1-Butyne
In organic chemistry, an alkyne is an unsaturated hydrocarbon containing at least one carbon—carbon triple bond. The simplest acyclic alkynes with only one triple bond and n ...
end with another equivalent of benzoylchloride gives the dicarbonyl, a precursor to an
oxazole
Oxazole is the parent compound for a vast class of heterocyclic compound, heterocyclic aromatic organic compounds. These are azoles with an oxygen and a nitrogen separated by one carbon. Oxazoles are aromatic compounds but less so than the thiaz ...
.
[''A new consecutive three-component oxazole synthesis by an amidation–coupling–cycloisomerization (ACCI) sequence'' Eugen Merkul and Thomas J. J. Müller ]Chem. Commun.
''ChemComm'' (or ''Chemical Communications''), formerly known as ''Journal of the Chemical Society D: Chemical Communications'' (1969–1971), ''Journal of the Chemical Society, Chemical Communications'' (1972–1995), is a peer-reviewed scientific ...
, 2006, 4817 - 4819,
:
Drugs
Propargylamine is used in the synthesis of:
#
Etintidine 9539-53-3br>
2-PAT#HDAC1/MAO-B-IN-1
759855-37-1
References
Aldehyde dehydrogenase inhibitors
Amines
Human drug metabolites
Propargyl compounds
{{Amine-stub