Synthesis of alkaloid-like compounds via the bridging Ritter reactions II

Ung, AT; West, AN; Phillips, MJA; Williams, SG

Synthesis of alkaloid-like compounds via the bridging Ritter reactions II

Ung, AT

West, AN Phillips, MJA Williams, SG

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Publication Type:: Journal Article
Citation:: Monatshefte fur Chemie, 2016, 147 (10), pp. 1737 - 1746
Issue Date:: 2016-10-01

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Field	Value	Language
dc.contributor.author	Ung, AT https://orcid.org/0000-0002-5665-0702	en_US
dc.contributor.author	West, AN	en_US
dc.contributor.author	Phillips, MJA	en_US
dc.contributor.author	Williams, SG https://orcid.org/0000-0003-4647-436X	en_US
dc.date.issued	2016-10-01	en_US
dc.identifier.citation	Monatshefte fur Chemie, 2016, 147 (10), pp. 1737 - 1746	en_US
dc.identifier.issn	0026-9247	en_US
dc.identifier.uri	http://hdl.handle.net/10453/51321
dc.description.abstract	© 2016, Springer-Verlag Wien. Abstract: The bridging Ritter reactions are considered to be efficient synthetic methods rapidly providing access to alkaloid-like compounds in a few steps from inexpensive starting materials. In this manuscript, we report the synthesis of benzo[c]azepine derivatives bearing either amide or hydroxyl groups via the bridging Ritter reactions. These compounds are diastereoisomers of a known AChE inhibitor. All the structures were fully characterised by NMR spectroscopy and high-resolution mass spectrometry. NMR spectral analysis of diastereoisomers has allowed for the relative stereochemistry of the AChE inhibitor to be established. Graphical abstract: [Figure not available: see fulltext.]	en_US
dc.relation.ispartof	Monatshefte fur Chemie	en_US
dc.relation.isbasedon	10.1007/s00706-016-1817-4	en_US
dc.subject.classification	General Chemistry	en_US
dc.title	Synthesis of alkaloid-like compounds via the bridging Ritter reactions II	en_US
dc.type	Journal Article
utslib.citation.volume	10	en_US
utslib.citation.volume	147	en_US
utslib.for	030402 Biomolecular Modelling and Design	en_US
utslib.for	0305 Organic Chemistry	en_US
utslib.for	03 Chemical Sciences	en_US
pubs.embargo.period	Not known	en_US
pubs.organisational-group	/University of Technology Sydney
pubs.organisational-group	/University of Technology Sydney/Faculty of Science
pubs.organisational-group	/University of Technology Sydney/Faculty of Science/School of Mathematical and Physical Sciences
pubs.organisational-group	/University of Technology Sydney/Strength - CCET - Centre for Clean Energy Technology
utslib.copyright.status	closed_access
pubs.issue	10	en_US
pubs.publication-status	Published	en_US
pubs.volume	147	en_US

Abstract:

© 2016, Springer-Verlag Wien. Abstract: The bridging Ritter reactions are considered to be efficient synthetic methods rapidly providing access to alkaloid-like compounds in a few steps from inexpensive starting materials. In this manuscript, we report the synthesis of benzo[c]azepine derivatives bearing either amide or hydroxyl groups via the bridging Ritter reactions. These compounds are diastereoisomers of a known AChE inhibitor. All the structures were fully characterised by NMR spectroscopy and high-resolution mass spectrometry. NMR spectral analysis of diastereoisomers has allowed for the relative stereochemistry of the AChE inhibitor to be established. Graphical abstract: [Figure not available: see fulltext.]

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http://hdl.handle.net/10453/51321