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

Tobias Seitz, Peng Fu, Franz Lucas Haut, Lutz Adam, Marija Habicht, Dieter Lentz, John B. MacMillan, Mathias Christmann

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

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.

Original languageEnglish (US)
Pages (from-to)3070-3073
Number of pages4
JournalOrganic Letters
Volume18
Issue number13
DOIs
StatePublished - Jul 1 2016

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Nuclear magnetic resonance
nuclear magnetic resonance
shift
synthesis
carboxylates
Chlorides
Condensation
condensation
chlorides
Derivatives
acids
Temperature
temperature
thiasporine A
bromopyruvate

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

One-Pot Synthesis of 5-Hydroxy-4H-1,3-thiazin-4-ones : Structure Revision, Synthesis, and NMR Shift Dependence of Thiasporine A. / Seitz, Tobias; Fu, Peng; Haut, Franz Lucas; Adam, Lutz; Habicht, Marija; Lentz, Dieter; MacMillan, John B.; Christmann, Mathias.

In: Organic Letters, Vol. 18, No. 13, 01.07.2016, p. 3070-3073.

Research output: Contribution to journalArticle

Seitz, Tobias ; Fu, Peng ; Haut, Franz Lucas ; Adam, Lutz ; Habicht, Marija ; Lentz, Dieter ; MacMillan, John B. ; Christmann, Mathias. / One-Pot Synthesis of 5-Hydroxy-4H-1,3-thiazin-4-ones : Structure Revision, Synthesis, and NMR Shift Dependence of Thiasporine A. In: Organic Letters. 2016 ; Vol. 18, No. 13. pp. 3070-3073.
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