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Reactions of 3,3,3-trifluoropyruvates with amidines — New trifluoromethyl substituted heterocyclic “building blocks”

Reaktion von 3,3,3-Trifluorbrenztraubensäureestern mit Amidinen. Neue trifluormethylsubstituierte heterocyclische „Building Blocks“

  • Organische Chemie Und Biochemie
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Summary

4-Hydroxy-4-trifluoromethyl-2-imidazolin-5-ones are obtained in good yields upon reaction of 3,3,3-trifluoropyruvates with amidines. Subsequent treatment of these heterocycles with thionyl chloride gives 4-chloro-4-trifluoromethyl-2-imidazolin-5-ones which proved to be versatile trifluoromethyl substituted building blocks. Substitution of chloride is feasible with a variety of hetero and carbon nucleophiles. Ring expansion with diazo compounds affords trifluoromethyl substituted pyrimidines.

Zusammenfassung

Bei der Reaktion von 3,3,3-Trifluorbrenztraubensäureestern mit Amidinen werden in guten Ausbeuten 4-Hydroxy-4-trifluormethyl-2-imidazolin-5-one gebildet. Durch Behandlung mit Thionylchlorid werden daraus 4-Chlor-4-trifluormethyl-2-imidazolin-5-one erhalten, die vielseitige trifluormethylsubstituierte Synthesebausteine darstellen. Der an C-4 gebundene Chlorsubstituent kann durch eine Vielzahl von Hetero- und Kohlenstoffnucleophilen ersetzt werden; mit Diazoverbindungen werden im Rahmen einer Ringerweiterungsreaktion trifluormethylsubstituierte Pyrimidine zugänglich.

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  1. Organisch-Chemisches Institut, Technische Universität München, Lichtenbergstr. 4, D-85748, Garching, Germany

    N. Sewald & K. Burger

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  1. N. Sewald
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  2. K. Burger
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Sewald, N., Burger, K. Reactions of 3,3,3-trifluoropyruvates with amidines — New trifluoromethyl substituted heterocyclic “building blocks”. Monatsh Chem 124, 899–907 (1993). https://doi.org/10.1007/BF00816413

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