Efficient one-pot quinoline derivative synthesis from acetophenone and allyl alcohols

Area of Science:

• Organic Chemistry
• Synthetic Chemistry

Background:

• Quinoline derivatives are crucial scaffolds in pharmaceuticals, agrochemicals, and functional materials.
• Developing efficient and selective synthetic methods for quinolines remains a significant challenge in organic chemistry.

Purpose of the Study:

• To introduce a novel strategy for site-selective ortho C-H functionalization and cyclization of acetophenones with allyl alcohols.
• To utilize O-sulfonylhydroxylamine (HOSA) as a transient directing group (TDG) for the construction of quinoline derivatives.

Main Methods:

• Employing O-sulfonylhydroxylamine (HOSA) as a catalytic transient directing group (TDG).
• Performing site-selective ortho C-H functionalization/cyclization of acetophenones with allyl alcohols in a one-pot process.
• Investigating the influence of TDG structure, solvent, and temperature on reaction pathway and selectivity.

Main Results:

• Achieved efficient construction of the quinoline scaffold under mild and tunable conditions.
• Demonstrated precise control over product selectivity by optimizing reaction parameters.
• Showcased broad substrate scope and excellent functional group tolerance for the developed method.

Conclusions:

• Presented the first application of HOSA as an efficient and versatile catalytic TDG in C-H cyclization reactions.
• Provided a practical and valuable synthetic route for diverse quinoline derivatives.
• Highlighted the potential of this methodology for accessing complex quinoline-based molecules.