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Synfacts 2009(6): 0601-0601
DOI: 10.1055/s-0029-1216701
DOI: 10.1055/s-0029-1216701
Synthesis of Heterocycles
© Georg Thieme Verlag
Stuttgart ˙ New York
Palladium-Catalyzed Cascade Synthesis of Pyrrolobenzazepines
V. Aureggi, M. Davoust, K. M. Gericke, M. Lautens*
University of Toronto, Canada
Further Information
Publication History
Publication Date:
25 May 2009 (online)


Significance
Reported is a one-pot, multistep process which provides a simple synthesis of pyrrolobenzazepines. The mechanism proposed progresses via ortho-alkylation to tether the alkyl chain to the aromatic ring, alkyne carbo-palladation to form the six-membered ring, and finally C-H activation to form the seven-membered ring. In the case of the pyrrole-based systems, interesting byproducts A and B were formed. The amounts could be altered by increasing the equivalents of norbornene. No further optimization studies were conducted. This type of norbornene-mediated multistep reaction is having a major impact in synthetic organic chemistry.