Dihydropyridine-based multicomponent reactions. Efficient entry into new tetrahydroquinoline systems through Lewis acid-catalyzed formal [4 + 2] cycloadditions

Org Lett. 2003 Mar 6;5(5):717-20. doi: 10.1021/ol027545d.

Abstract

The three-component reaction of dihydropyridines, aldehydes, and p-methylaniline efficiently forms highly substituted tetrahydroquinolines in a stereoselective manner through a Lewis acid-catalyzed formal [4 + 2] cycloaddition. InCl(3) and Sc(OTf)(3) are the catalysts of choice for this process. The in situ generation of a reactive 1,4-dihydropyridine through the regioselective nucleophilic addition of cyanide to pyridinium salts allows a one-pot four-component transformation.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry
  • Aniline Compounds / chemistry
  • Cyclization
  • Dihydropyridines / chemistry*
  • Quinolines / chemical synthesis*
  • Stereoisomerism

Substances

  • Aldehydes
  • Aniline Compounds
  • Dihydropyridines
  • Quinolines
  • methylaniline