Journal
TETRAHEDRON LETTERS
Volume 49, Issue 29-30, Pages 4542-4545Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2008.05.050
Keywords
click chemistry; privileged structures; sonogashira coupling; 1,3,5-triazines
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Introduction of the acetylene group on the 1,3,5-triazine scaffold was studied under various conditions. We describe here a new method to functionalize a triazine ring using Sonogashira coupling between 2-benzylsulfanyl-4,6-dichloro-1,3,5-triazine and trimethylsilylacetylene to give the corresponding 2-benzylsulfanyl-4-chloro-6-(trimethylsilyl)ethynyl-1,3,5-triazine. The latter was then used to obtain phosphoric acid mono-{4-[4-(4-amino-6-benzylsulfanyl-1,3,5-triazin-2-yl)-1,2,3-triazol-1-yl]-phenyl} ester via click chemistry by Huisgen 1,3-dipolar cycloaddition reaction. (c) 2008 Elsevier Ltd. All rights reserved.
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