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Synthesis 1993; 1993(9): 876-880
DOI: 10.1055/s-1993-25961
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Efficient Synthesis of 2,3,4,5-Tetrahydro-1H-3-benzazepines by Intramolecular Heck Reaction

Lutz F. Tietze* , Ralph Schimpf
  • *Institut für Organische Chemie der Universität Göttingen, Tammannstraße 2, D-3400 Göttingen, Germany
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Publikationsdatum:
29. April 2002 (online)

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A new facile method for the synthesis of the pharmacologically interesting 3-benzazepine skeleton is described. The easily available iodinated benzene derivative 3 is alkylated with allyl halides 4a-c to afford compounds 5a-c. Pd-catalyzed Heck-type cyclization leads to 3-benzazepines 6, 7, and 8 in 75-92 % yield, with 7 and 8 being mixtures of isomers. Hydrogenation gives uniform 1-alkyl substituted compounds 9a-c, of which 9c is transformed into the derivatives 10, 11, and 12.