Hickey, S.M.Ashton, T.D.Pfeffer, F.M.2025-12-172025-12-172015Asian Journal of Organic Chemistry, 2015; 4(4):320-3262193-58072193-5815https://hdl.handle.net/11541.2/116941Data source: Supporting Information, http://onlinelibrary.wiley.com.access.library.unisa.edu.au/doi/10.1002/ajoc.201402242/suppinfoThree 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.enCopyright 2015 Wiley-VCHbis(boc)aminoalkylguanidinesconvergent synthesisguanidinesynthetic methodsJournal article10.1002/ajoc.2014022422-s2.0-84927035666Hickey, S.M. [0000-0002-3063-531X]