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One-Pot Solvent-Involved Synthesis of 5-O-Substituted 5H-Chromeno[2,3-b]pyridines
Yuliya E Ryzhkova1, Fedor V Ryzhkov1, Michail N Elinson1
1N. D. Zelinsky Institute of Organic Chemistry Russian Academy of Sciences, 47 Leninsky Prospekt, 119991 Moscow, Russia.
Molecules (Basel, Switzerland)
|January 8, 2023
Summary
This study introduces a green chemistry approach for synthesizing novel O-substituted 5-alkoxy-5H-chromeno[2,3-b]pyridines using a one-pot, solvent-involved reaction. The efficient method yields high product amounts with a simple work-up procedure.
Area of Science:
- Organic Chemistry
- Green Chemistry
- Medicinal Chemistry
Background:
- Chromeno[2,3-b]pyridines are valuable heterocyclic compounds in medicinal and material science.
- Green chemistry principles, including Pot, Atom, and Step Economy (PASE), are crucial for sustainable synthesis.
- One-pot reactions minimize waste and improve efficiency in chemical synthesis.
Purpose of the Study:
- To develop a novel one-pot synthesis for O-substituted 5-alkoxy-5H-chromeno[2,3-b]pyridines.
- To enhance the PASE approach by incorporating component economy through solvent-involved reactions.
- To explore mechanistic insights and optimize reaction conditions for efficient synthesis.
Main Methods:
- A two-step transformation within a single pot, reacting salicylaldehydes with malononitrile dimer, followed by alcohol addition.
- Utilizing the solvent as a reactant, embodying component economy.
- Mechanistic studies to understand reaction pathways and optimize conditions.
- Structure confirmation using 2D NMR spectroscopy.
Main Results:
- Successful synthesis of previously unknown O-substituted 5-alkoxy-5H-chromeno[2,3-b]pyridines.
- Achieved high yields ranging from 77% to 93% through optimized reaction conditions.
- Demonstrated the efficiency and speed of the one-pot reaction.
- A convenient work-up procedure involving simple filtration.
Conclusions:
- The developed one-pot, solvent-involved reaction offers an efficient and green route to novel chromeno[2,3-b]pyridine derivatives.
- This approach aligns with PASE principles, offering a sustainable alternative for heterocyclic compound synthesis.
- The method is rapid, provides high yields, and features a simple isolation process, making it attractive for further applications.
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