Isoxazole Formation Mechanism

In summary, the student is having trouble uploading their work and is asking for a mechanism to convert furoxan with phenylacetylene and DMF to create isoxazole. They mention the possibility of using 1,3-dipolar cycloaddition but are concerned about unsymmetrical substitution. A reference to furoxan isomerization is provided.
  • #1
Natalie456
16
2
Homework Statement
Provide a mechanism for the conversion of the furoxan with phenylacetylene and DMF to create the isoxazole.
Relevant Equations
1,3 - dipolar cycloaddition?
Screen Shot 2020-02-23 at 2.38.28 AM.png

I'm having difficulties uploading my work to this system at the moment, but I have currently attempted 1,3-cycloaddition between the furoxan and phenylacetylene. However, unless a sigmatropic rearrangement occurs (which, as far as I can conclude, leads to instability with charges), this places the methyl and phenyl groups in the incorrect places. Is there a better way to, perhaps, go about this mechanism? Thank you.
 
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  • #2
Natalie456 said:
Homework Statement:: Provide a mechanism for the conversion of the furoxan with phenylacetylene and DMF to create the isoxazole.
Relevant Equations:: 1,3 - dipolar cycloaddition?

I'm having difficulties uploading my work to this system at the moment
Yeah unfortunately there aren't really any good options.

The only thing I can think to help you out with your question is that unsymmetrically substituted furoxans can sometimes isomerize between the two forms:
furoxan isomerization.png

This form gets you closer with 1,3-dipolar cycloaddition.

Edit: here's a reference to furoxan isomerization:
https://link.springer.com/article/10.1007/BF00519947

Further edit: obviously the tetravalent nitrogens have a +1 formal charge. Dunno why the drawing program didn't take care of that automatically.
 
Last edited:

What is the isoxazole formation mechanism?

The isoxazole formation mechanism is the chemical process by which an isoxazole compound is created. Isoxazoles are five-membered heterocycles with the formula C3H3NO. These compounds have a characteristic nitrogen-oxygen-nitrogen (N-O-N) ring structure and are commonly found in various natural products and pharmaceuticals.

What are the steps involved in the isoxazole formation mechanism?

The isoxazole formation mechanism typically involves three main steps: (1) the formation of an α-nitrile ketone intermediate, (2) the cyclization of the intermediate to form an α-nitroso ketone, and (3) the reduction of the nitroso group to form the final isoxazole product. These steps may vary depending on the specific reaction conditions and reactants used.

What are the key factors that influence the isoxazole formation mechanism?

The isoxazole formation mechanism is influenced by several factors, including the nature of the starting materials, the choice of catalyst or reagents, the reaction conditions (e.g. temperature, solvent, etc.), and the presence of any functional groups that may promote or inhibit the reaction. Additionally, the stereochemistry of the starting materials can also play a role in the outcome of the reaction.

What are some common applications of the isoxazole formation mechanism?

The isoxazole formation mechanism is a widely used method for the synthesis of isoxazole compounds, which have a variety of applications in medicinal chemistry, agricultural chemistry, and materials science. For example, isoxazole-containing compounds have been found to exhibit antimicrobial, antitumor, and anti-inflammatory properties, making them potential candidates for drug development.

Are there any challenges or limitations associated with the isoxazole formation mechanism?

One of the main challenges associated with the isoxazole formation mechanism is the potential for side reactions, which can lead to the formation of undesired by-products. Additionally, the use of toxic or expensive reagents and the need for specialized equipment or techniques may also pose limitations. Furthermore, the selectivity and yield of the reaction may vary depending on the specific reaction conditions and substrates used.

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