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

doi:10.1021/acs.orglett.6b01166

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 journal › Article › peer-review

21 Scopus citations

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 language	English (US)
Pages (from-to)	3070-3073
Number of pages	4
Journal	Organic Letters
Volume	18
Issue number	13
DOIs	https://doi.org/10.1021/acs.orglett.6b01166
State	Published - Jul 1 2016

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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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.",

author = "Tobias Seitz and Peng Fu and Haut, {Franz Lucas} and Lutz Adam and Marija Habicht and Dieter Lentz and MacMillan, {John B.} and Mathias Christmann",

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T2 - Structure Revision, Synthesis, and NMR Shift Dependence of Thiasporine A

AU - Seitz, Tobias

AU - Fu, Peng

AU - Haut, Franz Lucas

AU - Adam, Lutz

AU - Habicht, Marija

AU - Lentz, Dieter

AU - MacMillan, John B.

AU - Christmann, Mathias

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AB - 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.

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

Abstract

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