Efficient Synthesis of 2,3,4,5-Tetrahydro-1H-3-benzazepines by Intramolecular Heck Reaction
- 1 January 1993
- journal article
- research article
- Published by Georg Thieme Verlag KG in Synthesis
- Vol. 1993 (09) , 876-880
- https://doi.org/10.1055/s-1993-25961
Abstract
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.Keywords
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