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 0040-4020Full text not available in this repository. (Request a copy from the Strathclyde author)
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.
|Keywords:||dipolar cycloaddition, thiocarbonyl ylide, azomethine ylide, pyrrolo[1,2-c]thiazole, pyrazolo[1,5-c]thiazole, frontier MO theory, thiazole system, parameters, Pharmacy and materia medica, Biochemistry, Organic Chemistry, Drug Discovery|
|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:||04 May 2016 19:00|