Facile synthesis of guanidine functionalised building blocks
Date
2015
Authors
Hickey, S.M.
Ashton, T.D.
Pfeffer, F.M.
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Journal article
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Asian Journal of Organic Chemistry, 2015; 4(4):320-326
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Abstract
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.
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Data source: Supporting Information, http://onlinelibrary.wiley.com.access.library.unisa.edu.au/doi/10.1002/ajoc.201402242/suppinfo
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Copyright 2015 Wiley-VCH