Synthesis of isoquinoline-1,3(2H,4H)-dione derivatives via cascade reactions of N-alkyl-N-methacryloyl benzamide with aryl aldehydes

Org Biomol Chem. 2014 Oct 21;12(39):7690-3. doi: 10.1039/c4ob01442a. Epub 2014 Aug 29.

Abstract

A cascade reaction between N-alkyl-N-methacryloylbenzamide and aryl aldehydes was developed to generate isoquinoline-1,3(2H,4H)-dione derivatives. The reaction involves oxidative cross-coupling of the activated alkene from the N-alkyl-N-methacryloylbenzamide with the aldehyde functional group (-CHO), followed by radical addition to the aromatic ring to afford isoquinoline-1,3(2H,4H)-dione derivatives in good yields under mild reaction conditions without either metal catalysts or organic solvents involved.

MeSH terms

  • Aldehydes / chemistry*
  • Benzamides / chemistry*
  • Chemistry Techniques, Synthetic
  • Isoquinolines / chemical synthesis*
  • Isoquinolines / chemistry*

Substances

  • 1,3(2H,4H)-isoquinolinedione
  • Aldehydes
  • Benzamides
  • Isoquinolines
  • benzamide