Tethered Blatter Radical for Molecular Grafting: Synthesis of 6-Hydroxyhexyloxy,Hydroxymethyl, and Bis(hydroxymethyl) Derivatives and Their Functionalization |
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| Authors: | Szymon Kapuś ciń ski,Bindushree Anand,Paulina Bartos,Jose M. Garcia Fernandez,Piotr Kaszyń ski |
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| Affiliation: | 1.Faculty of Chemistry, University of Łódź, Tamka 12, 91-403 Łódź, Poland; (S.K.); (P.B.);2.Centre for Molecular and Macromolecular Studies, Polish Academy of Sciences, Sienkiewicza 112, 90-363 Łódź, Poland;3.Institute for Chemical Research, CSIC, University of Sevilla, Americo Vespucio 49, 41092 Sevilla, Spain;4.Department of Chemistry, Middle Tennessee State University, Murfreesboro, TN 37132, USA |
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| Abstract: | Synthetic access to 7-CF3-1,4-dihydrobenzo[e][1,2,4]triazin-4-yl radicals containing 4-(6-hydroxyhexyloxy)phenyl, 4-hydroxymethylphenyl or 3,5-bis(hydroxymethyl)phenyl groups at the C(3) position and their conversion to tosylates and phosphates are described. The tosylates were used to obtain disulfides and an azide with good yields. The Blatter radical containing the azido group underwent a copper(I)-catalyzed azide–alkyne cycloaddition with phenylacetylene under mild conditions, giving the [1,2,3]triazole product in 84% yield. This indicates the suitability of the azido derivative for grafting Blatter radical onto other molecular objects via the CuAAC “click” reaction. The presented derivatives are promising for accessing surfaces and macromolecules spin-labeled with the Blatter radical. |
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| Keywords: | heterocycles, stable radicals, functional group transformation, azide– alkyne “ click” reaction |
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