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Facile synthesis of guanidine functionalised building blocks

Hickey, Shane M., Ashton, Trent D. and Pfeffer, Frederick M. 2015, Facile synthesis of guanidine functionalised building blocks, Asian journal of organic chemistry, vol. 4, no. 4, pp. 320-326, doi: 10.1002/ajoc.201402242.

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Title Facile synthesis of guanidine functionalised building blocks
Author(s) Hickey, Shane M.
Ashton, Trent D.ORCID iD for Ashton, Trent D. orcid.org/0000-0002-6707-6064
Pfeffer, Frederick M.ORCID iD for Pfeffer, Frederick M. orcid.org/0000-0002-5441-6437
Journal name Asian journal of organic chemistry
Volume number 4
Issue number 4
Start page 320
End page 326
Total pages 7
Publisher Wiley
Place of publication Weinheim, Germany
Publication date 2015-01-01
ISSN 2193-5807
Keyword(s) Bis(Boc)aminoalkylguanidines
Convergent synthesis
Guanidine
Synthetic methods
Science & Technology
Physical Sciences
Chemistry, Organic
Chemistry
HGCL2-PROMOTED GUANYLATION REACTION
TRANSDUCTION DOMAIN MIMICS
PROTECTED GUANIDINES
PEPTIDE-SYNTHESIS
CHIRAL GUANIDINE
AMINO-ACIDS
ALPHA
INHIBITORS
REAGENTS
BINDING
Summary Three useful developments in the preparation of guanidines are presented herein. A collection of bis(Boc)aminoalkylguanidines (n=2, 3, 4 and 6; Boc=tert-butoxycarbonyl), known to be prone to cyclisation, have been synthesised and isolated without chromatography as shelf-stable sulfonate salts in good yield (up to 94%). Secondly, a selection of guanidines tethered to a range of other functional groups, including alkyne, alkene, alcohol, and azide, have been prepared in good yields with no requirement for a purification step, and thirdly an inexpensive, high-yielding (93%), and facile synthesis of N,N'-bis(Boc)guanidine, a key precursor for N,N'-bis(Boc)-N'-triflylguanidine, is described in which the need for chromatographic purification is again obviated.
Language eng
DOI 10.1002/ajoc.201402242
Field of Research 030503 Organic Chemical Synthesis
030401 Biologically Active Molecules
Socio Economic Objective 970103 Expanding Knowledge in the Chemical Sciences
HERDC Research category C1 Refereed article in a scholarly journal
Copyright notice ©2015, Wiley
Persistent URL http://hdl.handle.net/10536/DRO/DU:30075593

Document type: Journal Article
Collection: School of Life and Environmental Sciences
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Created: Fri, 27 Nov 2015, 09:54:10 EST

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