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Synlett 1998; 1998(2): 145-146
DOI: 10.1055/s-1998-1602
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Efficient Synthesis of Aza-Heterocycles by a Domino Process using an Inter- and an Intramolecular Heck Reaction

Lutz F. Tietze* , Raffaella Ferraccioli
  • *Institut für Organische Chemie, Georg-August-Universität Göttingen, Tammannstr. 2, D-37077 Göttingen, Germany; Fax [int] 49(0)5 51 39-94 76; E-mail: ltietze@gdwg.de
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Publication Date:
31 December 2000 (online)

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The palladium-catalyzed regioselective intermolecular Heck reaction of (Z)-2-(2-bromoethenyl)bromobenzene 6 and the cyclic enamide 9 gives 5 and 8 in an overall yield of 63%. Intramolecular Heck of 5 and 8, respectively leads to the tricyclic compounds 4 and 7, in 78% and 70% yields, respectively, which belong to two different classes of heterocyclic systems. The transformation can also be carried out as a domino process without isolation of the intermediates 5 and 8.

Heck reaction - domino reaction - palladium - benzoindole - benzoazepine