Preparation of new nitrogen-bridged heterocycles. 56. Syntheses and reactions of 1-[2,2-bis(alkylthio)-1-(ethoxycarbonylacetyl)vinyl]pyridinium salts

Chem Pharm Bull (Tokyo). 2004 Nov;52(11):1316-21. doi: 10.1248/cpb.52.1316.

Abstract

The title compounds, readily available from the S-alkylation of pyridinium 1-[alkylthio(thiocarbonyl)](ethoxycarbonylacetyl)methylides with alkyl halides or alkyl bromoacetates, were treated with a base and then a dehydrogenating agent to provide some unique products such as 3-[bis(alkylthio)methylene]-2(3H)-indolizinones and dialkyl 7-methyl-4-oxo-1,4,8,8a-tetrahydro-1,4-thiazino[3,4,5-cd]indolizine-1,5-dicarboxylates. On the other hand, similar reaction of these pyridinium salts in the absence of the dehydrogenating agent afforded alkyl 2-hydroxyindlizine-3-carboxythiolates, whose yields were increased by adding trifluoroacetic acid to the reaction mixture. The structures of some products were confirmed by the X-ray analyses.

MeSH terms

  • Heterocyclic Compounds / chemical synthesis*
  • Heterocyclic Compounds / metabolism
  • Nitrogen Compounds / chemical synthesis*
  • Nitrogen Compounds / metabolism
  • Pyridinium Compounds / chemical synthesis*
  • Pyridinium Compounds / metabolism
  • Salts / chemical synthesis*
  • Salts / metabolism

Substances

  • Heterocyclic Compounds
  • Nitrogen Compounds
  • Pyridinium Compounds
  • Salts