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Synthesis 1988; 1988(3): 199-203
DOI: 10.1055/s-1988-27511
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Über eine neue Methode zur positionsselektiven Einführung von Trifluormethyl-Gruppen in Heteroaromaten, Teil 3.1 Lineare und angulare Verknüpfung von Ringsystemen sowie Herstellung anellierter trifluormethyl-substituierter Fünfring-Heterocyclen.

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 3. Formation of Linearly and Angularly Coupled Ring Systems and Synthesis of Ring-fused Trifluoromethyl-1,3-azoles. Treatment of 4,4-bis(trifluoromethyl)-substituted hetero-1,3-dienes such as N-(hexafluoroisopropylidene)carboxamides, -thiocarboxamides, and (open-chain or hemicyclic) -amidines [e.g., 2-(hexafluoroisopropylidenamino) pyridines] with tin(II) chloride provides a new strategy for synthesis of coupled ring systems containing at least one 1,3-azole ring and of trifluoromethyl-substituted heterocyclic-fused 1,3-azoles such as imidazo[1,2-a]pyridines, imidazo[2,1-a]isoquinolines, imidazo [1,2-c]-pyrimidines, imidazo[1,2-a]pyrazines, imidazo[2,1-b]benzothiazoles, and imidazo[1,2-b][1,2,4]triazines.