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

Sutcliffe, O B and Storr, R C and Gilchrist, T L and Rafferty, P (2000) Cycloadditions to pyrrolo[1,2-c]thiazoles and pyrazolo[1,5-c]thiazoles. Tetrahedron, 56 (51). pp. 10011-10021. ISSN 0040-4020 (https://doi.org/10.1016/S0040-4020(00)00956-X)

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.

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• Item metadata

  Item type:	Article
  ID code:	31969
  Dates:	Date Event 15 December 2000 Published 6 December 2000 Published Online
  Subjects:	Medicine > Pharmacy and materia medica
  Department:	Faculty of Science > Strathclyde Institute of Pharmacy and Biomedical Sciences
  Depositing user:	Pure Administrator
  Date deposited:	13 Jul 2011 08:57
  Last modified:	11 Nov 2024 09:47
  URI:	https://strathprints.strath.ac.uk/id/eprint/31969