Facile Synthesis of Guanidine Functionalised Building Blocks. Issue 4 (19th January 2015)

• Record Type: Journal Article
• Authors: Hickey, Shane M.; Ashton, Trent D.; Pfeffer, Frederick M.
• Is Part Of: Asian journal of organic chemistry. Volume 4:Issue 4(2015:Apr.)
• Page Start: 320
• Page End: 326
• Publication Date: 2015-01-19
• Subjects: Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; 547.005
• DOI: 10.1002/ajoc.201402242
• Languages: English
• ISSNs: 2193-5807

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>Three useful developments in the preparation of guanidines are presented herein. A collection of bis(Boc)aminoalkylguanidines (<italic>n</italic>=2, 3, 4 and 6; Boc=<italic>tert</italic>‐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 <italic>N</italic>, <italic>N</italic>′‐bis(Boc)guanidine, a key precursor for <italic>N</italic>, <italic>N′</italic>‐bis(Boc)‐<italic>N</italic>′‐triflylguanidine, is described in which the need for chromatographic purification is again obviated.</p> </abstract>