Base-Promoted/Gold-Catalyzed Intramolecular Highly Selective and Controllable Detosylative Cyclization

Area of Science:

• Organic Chemistry
• Synthetic Chemistry

Background:

• Intramolecular cyclization reactions are fundamental in organic synthesis.
• Detosylative reactions offer unique pathways for C-C and C-N bond formation.
• Developing transition-metal-free or efficient catalytic methods is highly desirable.

Purpose of the Study:

• To develop a novel base-promoted intramolecular detosylative cyclization of bis-N-tosylhydrazones.
• To explore transition-metal-free and gold-catalyzed conditions for this transformation.
• To demonstrate the synthesis of nitrogen-containing heterocycles, cyclic olefins, and polycyclic aromatic compounds.

Main Methods:

• Base-promoted intramolecular cyclization of bis-N-tosylhydrazones.
• Gold(I)-catalyzed detosylative cyclization.
• Metal-free reaction conditions.

Main Results:

• Achieved highly selective and controllable detosylative cyclization of bis-N-tosylhydrazones.
• Synthesized various N-containing heterocycles and cyclic olefins.
• Developed an effective approach for synthesizing polycyclic aromatic compounds using metal-free or gold-catalyzed procedures.

Conclusions:

• The developed method provides a synthetically useful route to valuable organic scaffolds.
• The reaction is applicable under both transition-metal-free and gold-catalyzed conditions.
• This work expands the synthetic utility of bis-N-tosylhydrazones in organic synthesis.