Regioselective synthesis of new 2-(E)-cyano(thiazolidin-2-ylidene)thiazoles

Molecules. 2009 Nov 25;14(12):4849-57. doi: 10.3390/molecules14114849.

Abstract

Cyclocondensation of 2-[bis(methylthio)methylene]malononitrile (1) and cysteamine (2) afforded 2-(thiazolidin-2-ylidene)malononitrile (3). This compound on treatment with NaSH gave the corresponding thioamide derivative 4a in a regioselective manner on the basis of its single crystal X-ray diffraction analysis. Reaction of this compound with several alpha-bromocarbonyl compounds gave new 2-(E)-cyano(thiazolidin-2-ylidene)thiazoles 5a-g.

MeSH terms

  • Crystallography, X-Ray
  • Hydrogen Bonding
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Spectroscopy, Fourier Transform Infrared
  • Thiazoles / chemical synthesis*
  • Thiazoles / chemistry

Substances

  • Thiazoles