Abstract:
Isoxazolines and isoxazoles are used as intermediates to create important
functional groups. They also have practical uses such as the products soretolide, an
epileptic seizure medication, valdecoxib, an anti-inflammatory drug, muscimol, a GABA
receptor, and isoxaflutole, a pesticide. Finding a one-pot synthesis to produce
isoxazoline from an aldehyde will be time and resource efficient. The one-pot synthesis
then can be used for when doing a synthesis with an isoxazoline as an intermediate or
just to make isoxazoline products. The most successful type of aldehyde used to make
isoxazoline using one-pot synthesis is aromatic aldehydes without an alcohol group.
The specific aldehydes that were tested are anisaldehyde, 3,4,5-
trimethoxybenzaldehyde, and 3-nitrobenzaldehyde. The reactants used are
hydroxylamine hydrochloride, 10% sodium hydroxide, ethanol, water, allyl alcohol,
bleach, and dichloromethane. Aliphatic aldehydes like heptaldehyde and butrylaldehyde
were also tested. The only change in the procedure when using aliphatic aldehydes is
using 50% sodium hydroxide instead of 10% sodium hydroxide. Even though this
procedure would make isoxazoline, there was a large amount of impurities with little
isoxazoline. Further research would need to be done to find a better procedure to make
more isoxazoline.
