Synthesis of isomeric isothiazolo[4',3':4,5]- and isothiazolo[4',5':4,5]thieno[3,2-b]pyrano[2,3-d]pyridines by combination of domino reactions

ACS Comb Sci. 2013 Oct 14;15(10):541-5. doi: 10.1021/co400066y. Epub 2013 Sep 4.

Abstract

Isothiazolothienopyridines have been prepared by a domino reaction (the SN2 reaction → the Thorpe-Ziegler reaction → the Thorpe-Guareschi reaction type) from disodium 4-cyanoisothiazole-3,5-dithiolate. By changing the order of addition of the alkylation reagents in the reaction with disodium 4-cyanoisothiazole-3,5-dithiolate both possible isomers of the isothiazolothienopyridines are synthesized. These isomers were further used in three-component domino reaction (the Knoevenagel reaction → the Michael reaction → the hetero-Thorpe-Ziegler reaction type) to obtain wide range of isomeric isothiazolothienopyranopyridines.

MeSH terms

  • Combinatorial Chemistry Techniques
  • Models, Molecular
  • Molecular Structure
  • Pyrans / chemical synthesis*
  • Pyrans / chemistry
  • Pyridines / chemical synthesis*
  • Pyridines / chemistry
  • Stereoisomerism
  • Sulfhydryl Compounds / chemistry*
  • Thiazoles / chemical synthesis*
  • Thiazoles / chemistry
  • Thiophenes / chemical synthesis*
  • Thiophenes / chemistry

Substances

  • Pyrans
  • Pyridines
  • Sulfhydryl Compounds
  • Thiazoles
  • Thiophenes