Singh, Nimisha, et al. Journal of Materials Chemistry A 5.7 (2017): 3389-3403.
L-Thioproline (THP) has demonstrated significant potential in surface chemistry, particularly in the fabrication of self-assembled monolayers (SAMs) on gold substrates and gold nanoparticles (GNPs). SAMs of THP were successfully formed on gold wafers by immersing pre-cleaned gold surfaces in a 1 mM ethanolic solution of THP for 24 hours under anoxic conditions. The cleaning process involved sequential treatment with Piranha solution, ultrasonic baths in organic solvents, and nitrogen drying to ensure optimal monolayer formation. The resulting THP-functionalized gold wafers exhibited enhanced surface properties, making them suitable for applications in biosensing and nanotechnology.
THP was also used to modify GNPs by incubating a 5 mM aqueous THP solution with colloidal gold. The reaction led to a visible color change from red to dark purple, confirming the successful formation of THP-SAMs on GNPs. This modification of GNPs with THP provides a versatile platform for biofunctionalization, facilitating applications in targeted drug delivery, catalysis, and molecular recognition.
The ability of L-Thioproline to form stable SAMs on both planar and nanoparticulate gold surfaces highlights its significance in surface engineering. This approach opens avenues for the development of functionalized gold-based materials, with implications in biomedicine, diagnostics, and nanotechnology.
Barakat, Assem, et al. Molecules 26.23 (2021): 7276.
L-Thioproline has been employed as a crucial component in the regio- and diastereoselective synthesis of bi-spirooxindole-engrafted rhodanine analogs via a one-pot multicomponent [3 + 2] cycloaddition (32CA) reaction. This reaction involves the in situ generation of stabilized azomethine ylides (AYs) through the condensation of L-thioproline with 6-chloro-isatin, which subsequently reacts with an electron-deficient dipolarophile to yield the target spirocyclic products.
In a general synthetic protocol, L-thioproline (0.5 mmol) was refluxed with isatin derivatives and a rhodanine-based compound in an oil bath for 2 hours. Upon completion, slow evaporation at room temperature led to the precipitation of the desired bi-spirooxindole products as faint yellow solids with excellent yields (80-90%). Notably, the use of L-thioproline in this reaction enables high stereocontrol, facilitating the formation of well-defined spirocyclic architectures.
The successful application of L-thioproline in this multicomponent reaction underscores its significance in stereoselective synthesis. These bi-spirooxindole-rhodanine derivatives hold great promise for pharmaceutical and medicinal chemistry, particularly in the development of bioactive molecules with potential therapeutic applications.
Nafie, Mohamed S., et al. Frontiers in Chemistry 12 (2024): 1364378.
L-Thioproline plays a pivotal role in the efficient synthesis of spiro compounds, particularly bi-spirooxindole-incorporated rhodanine analogs. The synthesis proceeds through a one-pot multicomponent reaction involving L-thioproline, substituted isatin derivatives, and arylidene rhodanine analogs. The reaction is carried out under reflux in an oil bath for 2 hours in methanol, leading to the formation of highly stereoselective spiro compounds.
The method demonstrates excellent regioselectivity, where the azomethine ylide, generated from L-thioproline and isatin derivatives, undergoes a cycloaddition with arylidene rhodanine to yield the desired bi-spirooxindole structure. After the reaction, the crude mixture is allowed to evaporate at room temperature overnight, followed by filtration to obtain the final products with an impressive 80-90% yield.
L-Thioproline's unique properties, including its ability to form stable azomethine ylides, make it an essential reagent in the synthesis of complex spirocyclic molecules. These compounds, characterized by their faint yellow color, are of significant interest for their potential biological and pharmaceutical applications. This study highlights the utility of L-thioproline in advanced organic synthesis, demonstrating its versatility in the preparation of structurally intricate compounds with high yields.
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