Developed a metal-free method for synthesizing diverse quinolines, crucial in drug discovery. By combining alcohol, o-azido aldehyde, and alkyne using Lewis acid, we created a one-pot synthesis, forming C-C and C-N bonds efficiently. Our approach extends to cyclic ether-fused and sugar-derived quinolines. This method offers rapid access to bioactive compounds like graveoline and drug candidates. It provides a straightforward route to various derivatives, enhancing drug synthesis possibilities.
Figure (1) Biologically active 4-alkoxy quinoline pharmacophores.
Despite the importance of quinolines in drug discovery, existing methods for synthesizing them often involve multiple steps and low yields. There's a need for a simpler, more efficient approach to produce diverse quinoline derivatives, including cyclic ether-fused and sugar-derived ones
This metal-free, one-pot synthesis method enables the efficient and environmentally friendly production of quinolines without using transition metals. Through a multisegment cascade involving oxonium ion formation, C–C and C–N bond formation with alkynes, and optional allylation, the process offers a high-yielding and concise route to diverse quinoline derivatives. This approach is valuable for accessing pharmacophore analogs, drug candidates, and natural products with quinoline motifs.
A laboratory-scale prototype of the synthesis process has been successfully demonstrated. The method enables efficient one-pot synthesis of diverse functionalized quinolines, including bioactive molecules like graveoline, using a metal-free, oxonium ion-driven approach. The reactions have been validated in a research setting using standard organic chemistry techniques and reagents .
The technology has been granted a patent, and is currently available for licensing
3
- Enables Access to Medicinally Important Compounds: Facilitates synthesis of pharmacophores and drug molecules, potentially aiding in drug discovery.
- Sustainable and Environmentally Friendly Method: Metal-free protocol reduces environmental impact compared to traditional metal-catalyzed methods.
- Simplified Synthesis Process: One-pot allylation and cascade reactions offer a more straightforward approach, reducing time and resources.
- Expansion of Drug Development Avenues: Provides access to diverse quinoline derivatives, potentially leading to the development of new drugs.
- Potential for Economic Benefits: Offers a cost-effective synthesis route for important chemical compounds, benefiting pharmaceutical and chemical industries.
- Enhances Scientific Knowledge: Advances understanding of chemical reactions and synthesis strategies, contributing to scientific progress.
- Addressing Health Challenges: Production of bioactive molecules may contribute to addressing various health issues, including infectious diseases and inflammation.
Pharmaceuticals, Drug discovery, Medicinal chemistry, Chemical synthesis, Organic chemistry
Geography of IP
Type of IP
201621041730
434013