Demonstration of the feasibility of a direct solid-phase split-pool Biginelli synthesis of 3,4-dihydropyrimidinones

Org Lett. 2004 Sep 16;6(19):3237-40. doi: 10.1021/ol048946r.

Abstract

[reaction: see text] A direct, Lewis acid-catalyzed Biginelli synthesis of 3,4-dihydropyrimidinones has been performed on high-capacity polystyrene macrobeads with a polymer O-silyl-attached N-(3-hydroxypropyl)urea. Resin-urea was first reacted separately with either 4-bromo- or 4-chlorobenzaldehyde and LiOTf in MeCN at 80 degrees C. After washing, the beads were pooled and reacted with ethyl acetoacetate and LiOTf in MeCN at 80 degrees C. Formation of only one kind of Biginelli product per bead demonstrated the feasibility of a solid-phase non-Atwal two-step split-and-pool synthesis of 3,4-dihydropyrimidinones.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Catalysis
  • Indicators and Reagents
  • Molecular Structure
  • Pyrimidinones / chemical synthesis*
  • Temperature
  • Urea / analogs & derivatives
  • Urea / chemistry

Substances

  • Indicators and Reagents
  • Pyrimidinones
  • Urea