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Published on: June 10, 2021
Chromeno[2,3-d]pyrimidine-triones synthesis by a three-component coupling reaction
Ramin Ghahremanzadeh1, Fatemeh Fereshtehnejad, Ayoob Bazgir
1Department of Chemistry, Shahid Beheshti University, Tehran, Iran.
Chemical & Pharmaceutical Bulletin
|April 23, 2010
Summary
A new one-pot synthesis method efficiently creates chromeno[2,3-d]pyrimidine-triones using barbituric acids, aldehydes, and cyclohexane-1,3-diones. This reaction offers simplicity, good yields, and easy work-up, making it a valuable synthetic route.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
- Medicinal Chemistry
Background:
- Chromeno[2,3-d]pyrimidine derivatives are important scaffolds in medicinal chemistry.
- Efficient synthesis of these heterocyclic compounds is crucial for drug discovery.
- Existing synthetic methods may lack simplicity or require harsh conditions.
Purpose of the Study:
- To develop a simple and efficient one-pot synthesis for novel chromeno[2,3-d]pyrimidine-triones.
- To explore the scope of the reaction using various starting materials.
- To provide a facile route for library generation of these compounds.
Main Methods:
- A three-component condensation reaction involving barbituric acids, aldehydes, and cyclohexane-1,3-diones.
- The reaction was carried out in refluxing ethanol using p-toluenesulfonic acid (p-TSA) as a catalyst.
- Reaction times ranged from 3 to 10 hours.
Main Results:
- Successful synthesis of new chromeno[2,3-d]pyrimidine-triones was achieved.
- The method demonstrated operational simplicity and easy work-up procedures.
- Good yields were obtained across a range of tested substrates, validating the library approach.
Conclusions:
- The reported one-pot method provides a straightforward and efficient route to chromeno[2,3-d]pyrimidine-triones.
- This synthesis is suitable for generating diverse libraries of these heterocyclic compounds.
- The operational simplicity and good yields make this method attractive for further research and development.
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