Novel Synthesis of 4-Substituted Pyridine-2,6-Dicarboxylic Acid Derivatives (No. 0071)
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Summary
4-Substituted pyridine-2,6-dicarboxilic acids and their derivatives are important building blocks in the synthesis of bioactive molecules, chemical probes for biological research, solid-supported reagents and other functional molecules. However, known methods for the synthesis of 4-substituted pyridine-2,6-dicarboxylic acids derivatives often require long synthetic routes and harsh conditions. A team of OIST researchers led by Prof. Fujie Tanaka has developed a new synthetic protocol that overcomes the above problems and provides a simple one-pot method to unlock new derivatives.
Applications
- Therapeutic and preventative medicine
- Drug development
- Chemical probes for biological research
Advantages
- Mild conditions
- One-pot reaction
- High atom economy
The dihydro-2H-pyran precursor (1) can be readily synthesized in the same pot from aldehydes and pyruvates, which is also an OIST invention (OIST ref. 0023).
The OIST team built a library of novel 4-substituted pyridine-2,6-carboxylic acid derivatives
Click on the images to enlarge
Technology
This is a novel method to synthesize chemically and biologically important 4-substituted pyridine-2,6-dicarboxylic acid derivatives, whereby pyruvates and aldehydes are reacted with a pyrrolidine-acetic acid catalyst to form dihydropyran derivatives, which are further reacted with ammonium acetate in one pot under mild conditions to yield the desired products.
Media Coverage and Presentations
CONTACT FOR MORE INFORMATION
Paola Butler-Zanetti
Technology Licensing Section
tls@oist.jp
+81(0)98-966-8937