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Seven-Membered Rings
Citation
Smith, Jason and Molesworth, PP and Ryan, JH, Seven-Membered Rings, Progress in Heterocyclic Chemistry, Elsevier, G.W. Gribble and J.A. Joule (ed), Amsterdam, pp. 491-530. ISBN 978-0-08-096515-4 (2009) [Research Book Chapter]
DOI: doi:10.1016/S0959-6380(09)70044-3
Abstract
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.
Item Details
Item Type: | Research Book Chapter |
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Research Division: | Chemical Sciences |
Research Group: | Organic chemistry |
Research Field: | Organic chemical synthesis |
Objective Division: | Expanding Knowledge |
Objective Group: | Expanding knowledge |
Objective Field: | Expanding knowledge in the chemical sciences |
UTAS Author: | Smith, Jason (Associate Professor Jason Smith) |
UTAS Author: | Molesworth, PP (Dr Peter Molesworth) |
ID Code: | 62401 |
Year Published: | 2009 |
Deposited By: | Chemistry |
Deposited On: | 2010-03-11 |
Last Modified: | 2015-03-24 |
Downloads: | 0 |
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