Catalytic α-Oxidation of N-Acylated 1,3-Oxazolidin-2-ones with Molecular Oxygen
(2026) KEMR10 20251Department of Chemistry
- Abstract
- Introduction: Molecular oxygen is the most common oxidizer in nature. Since it has been
part of evolution, it is heavily incorporated into biological systems, the most significant being
cellular respiration, glycolysis, and the citric acid cycle. Luckily, molecular oxygen can also
be used as an oxidizer in the lab, and with the right conditions, to generate 1,2-dicarbonyl
compounds.
Background: Given that many proteins have developed an affinity for this type of compound,
several pharmaceuticals have been made with this functionality, to increase their
bioavailability. Examples are Indibulin, Biricodar, Boceprevir, and Fluocortin butyl.
Aim: The aim is to investigate if N-acylated 1,3-oxazolidin-2-ones can be catalytically... (More) - Introduction: Molecular oxygen is the most common oxidizer in nature. Since it has been
part of evolution, it is heavily incorporated into biological systems, the most significant being
cellular respiration, glycolysis, and the citric acid cycle. Luckily, molecular oxygen can also
be used as an oxidizer in the lab, and with the right conditions, to generate 1,2-dicarbonyl
compounds.
Background: Given that many proteins have developed an affinity for this type of compound,
several pharmaceuticals have been made with this functionality, to increase their
bioavailability. Examples are Indibulin, Biricodar, Boceprevir, and Fluocortin butyl.
Aim: The aim is to investigate if N-acylated 1,3-oxazolidin-2-ones can be catalytically and
selectively α-oxidized by non-harmful and abundant molecular oxygen via an in-situ formed
copper(II) complex with a high tolerance for a wide range of aromatic substrates, and to
explore how different nitrogen-based ligands affect this reaction.
Methods: To connect the methodology to more common starting materials, some of the
substrates will also be synthesized from 1,3-oxazolidin-2-one and the corresponding
carboxylic acid via the formation of a mixed anhydride. An objective is to fully characterize
the corresponding oxidated products by 1H NMR spectroscopy, 13C NMR spectroscopy, FTIR
spectroscopy, melting point, and HRMS.
Results: The reaction showed a high tolerance for a wide range of aromatic N-acylated 1,3
oxazolidin-2-ones, with a few exceptions where optimization is needed. A ligand screening
revealed that 1,10-phenanthroline was the best choice of ligand out of eleven tested.
Conclusion: The reaction is a good synthetic pathway to generate 1,2-dicarbonyl compounds,
and has also proven to be green due to its conditions and atom economy. (Less) - Popular Abstract
- Molecular oxygen is the most common oxidizer in nature and represents 21% of the air.
Since it has been part of evolution, it is heavily incorporated into biological systems, the most
significant being cellular respiration. Because of this, atomic oxygen is included in many
biological molecules, sometimes as a 1,2-dicarbonyl compound. These compounds can for
example be seen in the glycolysis and the citric acid cycle as pyruvate and α-ketoglutarate.
Given that many proteins have developed an affinity for this type of compound, several
pharmaceuticals have been made with this functionality, thereby increasing their
bioavailability. Luckily, molecular oxygen can also be used as an oxidizer in the lab, and
with the right... (More) - Molecular oxygen is the most common oxidizer in nature and represents 21% of the air.
Since it has been part of evolution, it is heavily incorporated into biological systems, the most
significant being cellular respiration. Because of this, atomic oxygen is included in many
biological molecules, sometimes as a 1,2-dicarbonyl compound. These compounds can for
example be seen in the glycolysis and the citric acid cycle as pyruvate and α-ketoglutarate.
Given that many proteins have developed an affinity for this type of compound, several
pharmaceuticals have been made with this functionality, thereby increasing their
bioavailability. Luckily, molecular oxygen can also be used as an oxidizer in the lab, and
with the right conditions, to generate said compounds. In this report, the aim is the
optimization and the scope of a catalytic α-oxidation reaction of imides with molecular
oxygen, copper(II) acetate, and a ligand. Results show that the reaction has a high tolerance
for a wide range of substrates, but that optimization is needed for substrates with unprotected groups. (Less)
Please use this url to cite or link to this publication:
http://lup.lub.lu.se/student-papers/record/9218325
- author
- Sundman, Tanja LU
- supervisor
- organization
- course
- KEMR10 20251
- year
- 2026
- type
- H2 - Master's Degree (Two Years)
- subject
- keywords
- 1, 2-dicarbonyl compounds, molecular oxygen, scaffold, metal enolate, catalysis, organic chemistry
- language
- English
- id
- 9218325
- date added to LUP
- 2026-01-13 11:09:43
- date last changed
- 2026-01-13 11:09:43
@misc{9218325,
abstract = {{Introduction: Molecular oxygen is the most common oxidizer in nature. Since it has been
part of evolution, it is heavily incorporated into biological systems, the most significant being
cellular respiration, glycolysis, and the citric acid cycle. Luckily, molecular oxygen can also
be used as an oxidizer in the lab, and with the right conditions, to generate 1,2-dicarbonyl
compounds.
Background: Given that many proteins have developed an affinity for this type of compound,
several pharmaceuticals have been made with this functionality, to increase their
bioavailability. Examples are Indibulin, Biricodar, Boceprevir, and Fluocortin butyl.
Aim: The aim is to investigate if N-acylated 1,3-oxazolidin-2-ones can be catalytically and
selectively α-oxidized by non-harmful and abundant molecular oxygen via an in-situ formed
copper(II) complex with a high tolerance for a wide range of aromatic substrates, and to
explore how different nitrogen-based ligands affect this reaction.
Methods: To connect the methodology to more common starting materials, some of the
substrates will also be synthesized from 1,3-oxazolidin-2-one and the corresponding
carboxylic acid via the formation of a mixed anhydride. An objective is to fully characterize
the corresponding oxidated products by 1H NMR spectroscopy, 13C NMR spectroscopy, FTIR
spectroscopy, melting point, and HRMS.
Results: The reaction showed a high tolerance for a wide range of aromatic N-acylated 1,3
oxazolidin-2-ones, with a few exceptions where optimization is needed. A ligand screening
revealed that 1,10-phenanthroline was the best choice of ligand out of eleven tested.
Conclusion: The reaction is a good synthetic pathway to generate 1,2-dicarbonyl compounds,
and has also proven to be green due to its conditions and atom economy.}},
author = {{Sundman, Tanja}},
language = {{eng}},
note = {{Student Paper}},
title = {{Catalytic α-Oxidation of N-Acylated 1,3-Oxazolidin-2-ones with Molecular Oxygen}},
year = {{2026}},
}