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Synthesis 1988; 1988(3): 189-194
DOI: 10.1055/s-1988-27509
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Über eine neue Methode zur positionsselektiven Einführung von Trifluormethyl-Gruppen in Heteroaromaten, Teil 1. Synthese von trifluormethyl-substituierten 1,3-Azolen (Oxazole, Thiazole, Imidazole)

Klaus Burger* , Klaus Geith, Dieter Hübl
  • *Institut für Organische Chemie der Technischen Universität München, Lichtenbergstraße 4, D-8046 Garching, Federal Republic of Germany
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Publication Date:
20 August 2002 (online)

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A New Method for Regioselective Introduction of Trifluoromethyl Groups into Heteroarenes; Part 1. Synthesis of Trifluoromethyl-substituted 1,3-Azoles (Oxazoles, Thiazoles, Imidazoles) The reaction of 4,4-bis(trifluoromethyl) -substituted hetero-1,3-dienes [N-(Hexafluoro-2-propylidene)carboxamides, -thiocarboxamides, and -amidines] with tin(II) chloride affords 5-fluoro-4-trifluoromethyl- oxazoles, -thiazoles, and -imidazoles, respectively. The reaction sequence involves heterocyclic tin(IV) compounds as intermediates.