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Two-Step Macrocycle Synthesis by Classical Ugi Reaction.

Eman M M Abdelraheem1,2, Samad Khaksar1, Katarzyna Kurpiewska3

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A novel two-step method enables direct nonpeptidic macrocycle synthesis using the Ugi four-component reaction (U-4CR). This efficient approach generates diverse macrocycles with varying ring sizes from readily available starting materials.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Medicinal Chemistry

Background:

  • Macrocycles are important scaffolds in medicinal chemistry.
  • Traditional macrocycle synthesis can be complex and low-yielding.
  • Developing efficient and versatile synthetic routes is crucial.

Purpose of the Study:

  • To introduce a direct nonpeptidic macrocycle synthesis method.
  • To establish an efficient two-step procedure for complex macrocycle construction.
  • To explore the diversity and scope of the developed synthetic approach.

Main Methods:

  • Utilizing the Ugi four-component reaction (U-4CR) for macrocyclization.
  • A two-step synthesis involving unprotected diamines and isocyanocarboxylic acids.
  • Subsequent U-4CR with diverse aldehydes and carboxylic acids in a one-pot procedure.

Main Results:

  • High yields of diverse, unprecedented building blocks in the first step.
  • Successful Ugi four-component reaction (U-4CR) of α-isocyano-ω-amines.
  • Generation of a wide range of macrocycles with varying ring sizes.

Conclusions:

  • The developed method offers a short, efficient, and flexible route to nonpeptidic macrocycles.
  • This approach provides access to diverse macrocyclic structures.
  • The Ugi four-component reaction is a powerful tool for macrocycle synthesis.