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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
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
Author:Smith, Jason (Associate Professor Jason Smith)
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
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