Ultrasonic-promoted three-component synthesis of some biologically active 1,2,5,6-tetrahydropyrimidines

J Comb Chem. 2007 Sep-Oct;9(5):797-803. doi: 10.1021/cc700089a. Epub 2007 Aug 1.

Abstract

Multicomponent reactions and organic synthesis with ultrasonic activation have been used as key methods for the synthesis of tetrahydropyrimidine derivatives. The three-component condensation of 1,3-diarylprop-2-en-1-one with ammonia and aldehydes/acetone or N-substituted gamma-pyridones under ultrasonic irradiation was developed as a rapid and efficient solution-phase method for the high-yielding preparation of 2-aryl(hetaryl)-4,6-diaryl-1,2,5,6-tetrahydropyrimidines and 2,4-diaryl-1,5,9-triazaspiro[5.5]undec-1-enes. The described synthetic protocol provides rapid access to novel and diversely substituted tetrahydropyrimidines libraries. The simple, primary biological screening showed 98% of inhibitory activity against Mycobacterium tuberculosis for one of tetrahydropyrimidines synthesized.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Antitubercular Agents / chemical synthesis*
  • Antitubercular Agents / pharmacology
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Mycobacterium tuberculosis / drug effects
  • Pyrimidines / chemical synthesis*
  • Pyrimidines / pharmacology
  • Spectrometry, Mass, Electrospray Ionization
  • Ultrasonics*
  • X-Ray Diffraction

Substances

  • Antitubercular Agents
  • Pyrimidines