One-Pot Synthesis of 5-Hydroxy-4H-1,3-thiazin-4-ones: Structure Revision, Synthesis, and NMR Shift Dependence of Thiasporine A.
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.
Institute of Chemistry and Biochemistry, Freie Universität Berlin , Takustraße 3, 14195 Berlin, Germany.
Tobias
T
Seitz
Department of Biochemistry, University of Texas Southwestern Medical Center at Dallas , Dallas, Texas 75390, United States.
Peng
P
Fu
Institute of Chemistry and Biochemistry, Freie Universität Berlin , Takustraße 3, 14195 Berlin, Germany.
Franz-Lucas
FL
Haut
Institute of Chemistry and Biochemistry, Freie Universität Berlin , Takustraße 3, 14195 Berlin, Germany.
Lutz
L
Adam
Institute of Chemistry and Biochemistry, Freie Universität Berlin , Takustraße 3, 14195 Berlin, Germany.
Marija
M
Habicht
Institute of Chemistry and Biochemistry, Freie Universität Berlin , Takustraße 3, 14195 Berlin, Germany.
Dieter
D
Lentz
Department of Biochemistry, University of Texas Southwestern Medical Center at Dallas , Dallas, Texas 75390, United States.
John B
JB
MacMillan
Institute of Chemistry and Biochemistry, Freie Universität Berlin , Takustraße 3, 14195 Berlin, Germany.
Mathias
M
Christmann
D002264:Carboxylic Acids / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013843:Thiazines / Q000138:chemical synthesis*; D013854:Thioamides / Q000737:chemistry
D002264:Carboxylic Acids; D013843:Thiazines; D013854:Thioamides; C000598673:thiasporine A