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Seven-Membered Rings
This chapter describes the chemistry of seven-membered heterocycles, with emphasis on research focussing on the construction and reactions of these heterocyclic systems. A continued trend has been to use seven-membered heterocyclic motifs in derivatives of biologically active molecules, and a summary of the key advancements in pharmacological activity of these derivatives is reviewed in the chapter. The chiral azepine are synthesized from phenylalanine by way of the alkenyl amine derivative that underwgoes oxidative cleavage and intramolecular reductive amination. Reductive amination is the method used for the formation of the azepine as a derivative of deoxynorjirimycin. Constrained phenylalanine derivatives are synthesised via an ene-yne metathesis that not only forms the azepine ring but gives a diene that is transformed into the fused benzoazepine. Azepines and heterocyclic fused derivatives are formed in good to moderate yields by the reaction of an enamine.
History
Publication title
Progress in Heterocyclic ChemistryVolume
21Editors
G.W. Gribble and J.A. JoulePagination
491-530ISBN
978-0-08-096515-4Department/School
School of Natural SciencesPublisher
ElsevierPlace of publication
AmsterdamExtent
8Repository Status
- Restricted