4.6 Article

Syntheses of quinazolinones from 2-iodobenzamides and enaminones via copper-catalyzed domino reactions

Journal

ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 12, Issue 26, Pages 4571-4575

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c4ob00400k

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Funding

  1. Thailand Research Fund [RTA5480002]
  2. Development and Promotion of Science and Technology Talents Project (DPST)
  3. Science Achievement Scholarship of Thailand (SAST)

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N-Substituted 2-iodobenzamides and enaminones undergo cascade transformations to achieve quinazolinones via a copper-catalyzed Ullmann-type coupling, a Michael addition and a retro-Mannich reaction. A unique stereochemical feature of this domino process was that Z-enaminones reacted without external ligands, whereas E-enaminones required the assistance of ligands.

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