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A Bifurcated Multicomponent Synthesis Approach to Polycyclic Quinazolinones.

Ruixue Xu1, Zefeng Wang1, Qiang Zheng1

  • 1Drug Design Group, Department of Pharmacy, University of Groningen, Groningen 9713, AV, The Netherlands.

The Journal of Organic Chemistry
|September 12, 2022
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Summary

Two novel Ugi four-component reaction (Ugi-4CR) strategies rapidly synthesize diverse polycyclic quinazolinones. These methods efficiently create complex, biologically relevant molecules with tailored properties in minimal steps.

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Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry
  • Synthetic Chemistry

Background:

  • Polycyclic quinazolinones are important scaffolds in medicinal chemistry.
  • Efficient synthesis of diverse quinazolinone derivatives is challenging.
  • Multi-component reactions (MCRs) offer a powerful approach for rapid molecular assembly.

Purpose of the Study:

  • To develop rapid and efficient synthetic routes to diverse substituted polycyclic quinazolinones.
  • To explore novel applications of the Ugi four-component reaction (Ugi-4CR) in quinazolinone synthesis.
  • To enable the construction of biologically interesting compounds with tailored properties.

Main Methods:

  • Two orthogonal Ugi-4CR-based protocols were developed.
  • Protocol 1: Ammonia-Ugi-4CR followed by palladium-catalyzed annulation.
  • Protocol 2: Ugi-4CR using cyanamide as the amine component, followed by radical cyclization.

Main Results:

  • Rapid synthesis of diverse substituted polycyclic quinazolinones was achieved.
  • Both developed protocols demonstrated high efficiency in constructing complex molecular architectures.
  • The cyanamide-based Ugi-4CR approach was unprecedented.
  • The methods allowed for tailored properties in the synthesized compounds.

Conclusions:

  • The developed Ugi-4CR-based protocols provide an efficient and rapid method for synthesizing diverse polycyclic quinazolinones.
  • These MCR and cyclization strategies offer a significant advantage over existing methods for accessing complex, biologically relevant molecules.
  • The synthetic routes enable the tailored design and construction of novel quinazolinone derivatives for potential therapeutic applications.