47. One-Pot Synthesis of 5-Hydroxy-4H-1,3-thiazin-4-ones: Structure Revision, Synthesis, and NMR Shift Dependence of Thiasporine A

T. Seitz, P. Fu, F.-L. Haut, L. Adam, M. Habicht, D. Lentz, J. B. MacMillan, M. Christmann

An annulation of arylthioamides with 3-bromopyruvic acid chloride to 5-hydroxy-4H-1,3-thiazin-4-ones has been developed. The initial condensation affords two regioisomeric thiazolinone intermediates in a temperature-dependent manner. The synthesis of the 2-aminophenylthiazinone derivative led to the revision of the previously proposed structure of thiasporine A. Synthesis of the revised structure and NMR analysis revealed that thiasporine A had been isolated as a carboxylate.

Title47. One-Pot Synthesis of 5-Hydroxy-4H-1,3-thiazin-4-ones: Structure Revision, Synthesis, and NMR Shift Dependence of Thiasporine A
AuthorT. Seitz, P. Fu, F.-L. Haut, L. Adam, M. Habicht, D. Lentz, J. B. MacMillan, M. Christmann
IdentifierDOI: 10.1021/acs.orglett.6b01166
Source(s)
CitationOrg. Lett. 2016, 18, 3070-3073