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Stable hemiaminals from axially chiral pyridine compounds
Senel Teke Tuncel1, Ilke Demir2, Safiye Sağ Erdem2
1Department of Chemistry, Bogazici University, Istanbul, Turkey.
Chirality
|February 10, 2023
Summary
Researchers synthesized novel pyridyl thiazolidin-4-ol derivatives regioselectively using lithium aluminum hydride. Restricted rotation led to M/P isomers, stabilized by intramolecular hydrogen bonding, confirmed by DFT studies.
Area of Science:
- Organic Chemistry
- Medicinal Chemistry
- Computational Chemistry
Background:
- Thiazolidin-4-one derivatives are important scaffolds in medicinal chemistry.
- Synthesis of novel heterocyclic compounds with potential biological activities is of great interest.
Purpose of the Study:
- To synthesize novel 3-(pyridin-2-yl)-2-(pyridin-2-ylimino)thiazolidin-4-ol derivatives.
- To investigate the stereochemical outcome and stabilization mechanisms of the synthesized compounds.
Main Methods:
- Regioselective synthesis of derivatives from 2-iminothiazolidin-4-ones.
- Utilized lithium aluminum hydride (LiAlH4) reduction at room temperature.
- Employed computational DFT studies to elucidate molecular interactions.
Main Results:
- Successfully synthesized a series of 3-(pyridin-2-yl)-2-(pyridin-2-ylimino)thiazolidin-4-ol derivatives.
- Observed the formation of M/P isomers due to restricted rotation around the N3-Caryl bond.
- Demonstrated intramolecular hydrogen bonding between the OH group and pyridyl nitrogen, stabilizing the molecule.
Conclusions:
- The synthesized pyridyl thiazolidin-4-ol derivatives exhibit interesting stereochemical properties.
- Intramolecular hydrogen bonding plays a crucial role in stabilizing the hemiaminal structure and preventing dehydration.
- The findings provide insights into the synthesis and stability of novel heterocyclic compounds.
Keywords:
2-iminothiazolidin-4-olaxially chiral hemiaminalintramolecular hydrogen bondingpyridine compoundsstable hemiaminalMore Related Videos
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