Cycloadditions to pyrrolo[1,2-c]thiazoles and pyrazolo[1,5-c]thiazoles

O B Sutcliffe, R C Storr, T L Gilchrist, P Rafferty

Research output: Contribution to journalArticle

24 Citations (Scopus)

Abstract

The pyrrolo[1,2-c]thiazole generated by dehydration of dimethyl 5-methyl-1H,3H-pyrrolo[1,2-c]thiazole-6,7-dicarboxylate 2-oxide acts as a thiocarbonyl ylide in its cycloaddition to electron deficient alkenes but as an azomethine ylide with electron deficient alkynes. The analogous pyrazolo[1,5-c]thiazole, generated similarly, acts as a thiocarbonyl ylide with both types of dipolarophile. This behaviour is partially explained by Frontier MO theory.

Original languageEnglish
Pages (from-to)10011-10021
Number of pages11
JournalTetrahedron
Volume56
Issue number51
Early online date6 Dec 2000
DOIs
Publication statusPublished - 15 Dec 2000

Keywords

  • dipolar cycloaddition
  • thiocarbonyl ylide
  • azomethine ylide
  • pyrrolo[1,2-c]thiazole
  • pyrazolo[1,5-c]thiazole
  • frontier MO theory
  • thiazole system
  • parameters

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    Sutcliffe, O. B., Storr, R. C., Gilchrist, T. L., & Rafferty, P. (2000). Cycloadditions to pyrrolo[1,2-c]thiazoles and pyrazolo[1,5-c]thiazoles. Tetrahedron, 56(51), 10011-10021. https://doi.org/10.1016/S0040-4020(00)00956-X