A Concise Approach to N-Substituted Rhodanines through a Base-Assisted One-Pot Coupling and Cyclization Process
Yongxi Liang1, Mei-Lin Tang1,2, Zhipeng Huo1
1Department of Natural Medicine, School of Pharmacy, Fudan University, 826 Zhangheng Road, Shanghai 201203, China.
Molecules (Basel, Switzerland)
|March 8, 2020
Summary
Researchers developed a new one-pot method for synthesizing functionalized rhodanines. This efficient process uses readily available starting materials and offers a scalable route to N-substituted rhodanines with high yields.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
- Medicinal Chemistry
Background:
- Rhodanine derivatives are important scaffolds in medicinal chemistry, exhibiting a wide range of biological activities.
- Efficient and scalable synthetic routes are crucial for accessing diverse libraries of N-substituted rhodanines for drug discovery.
- Existing methods for rhodanine synthesis may involve multiple steps or harsh conditions, limiting their applicability.
Purpose of the Study:
- To develop a novel, efficient, and one-pot synthetic strategy for the preparation of functionalized N-substituted rhodanines.
- To establish a scalable method that tolerates a broad range of functional groups.
- To provide a versatile route for accessing diverse rhodanine derivatives.
Main Methods:
- A base-assisted one-pot reaction involving the coupling and continuous cyclization of a primary amine, carbon disulfide, and methyl (2-chloroacetyl)carbamate.
- Optimization of reaction conditions to maximize yield and purity of the target N-substituted rhodanines.
- Demonstration of the method's tolerance to various functional groups present in the starting materials.
Main Results:
- Successful synthesis of functionalized N-substituted rhodanines via the developed one-pot procedure.
- The conversion demonstrated excellent yields across a broad range of substrates.
- The method proved to be scalable, facilitating the preparation of larger quantities of N-substituted rhodanines.
Conclusions:
- The developed base-assisted one-pot approach offers an efficient and versatile route to N-substituted rhodanines.
- This method is suitable for the scalable preparation of diverse functionalized rhodanines.
- The synthetic strategy's broad functional group tolerance enhances its utility in organic synthesis and medicinal chemistry.
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