Vanillic aldehydes for the one-pot synthesis of novel 2-oxo-1,2,3,4-tetrahydropyrimidines

Mol Divers. 2016 Aug;20(3):591-604. doi: 10.1007/s11030-016-9658-y. Epub 2016 Jan 30.

Abstract

A small library of novel 2-oxo-1,2,3,4-tetrahydropyrimidines was synthesized via a one-pot multicomponent Biginelli reaction. Copper complex [Formula: see text] which was used for the first time as a homogeneous and heterogeneous catalyst, makes this a facile and efficient reaction at room temperature. All the obtained products fall out of the solution in pure form and are easily isolated via filtration in good-to-excellent yields. The molecular structure of one of the products, ethyl 6-methyl-2-oxo-4-(4[Formula: see text]-isopropoxy-3[Formula: see text]-methoxyphenyl) - 1,2,3,4 - tetrahydropyrimidine-5- carboxylate, has been determined by X-ray crystallography. All non-hydrogen atoms in the heterocyclic, six-membered ring are determined to be approximately coplanar.

Keywords: Heterocycles; Heterogeneous catalysis; Homogeneous catalysis; Multicomponent reactions (MCRs).

MeSH terms

  • Aldehydes / chemistry*
  • Catalysis
  • Combinatorial Chemistry Techniques
  • Crystallography, X-Ray
  • Molecular Structure
  • Pyrimidines / chemical synthesis*
  • Pyrimidines / chemistry
  • Vanillic Acid / chemistry*

Substances

  • Aldehydes
  • Pyrimidines
  • Vanillic Acid