We report a highly efficient substitution reaction of 3-hydroxyoxindoles 1 using TMSN3 to furnish 3-substituted 3-azidooxindoles as the precursor of quaternary 3-aminooxindoles. Utility of this protocol has been revealed by synthesizing new classes of polyether systems and macrocyles embedded with the 1,2,3-triazole and 1,3-diyne units. ![]() ![]() In this method, Cu(OTf)2 served as a single catalyst for both the azidation of alcohol and click reaction steps. ![]() The second method involves Cu(OTf)2-catalyzed direct azidation of allylic/benzylic alcohols and their methyl ethers with TMSN3 as the first step followed by the click reaction of azides with alkynes as the second step. The first method involves magnetically separable nano Fe3O4-catalyzed direct azidation of various allylic/benzylic alcohols with TMSN3 as the first step followed by the Cu-catalyzed click reaction of azides with alkynes as the second step. Two methods involving sequential reactions were developed for synthesizing substituted 1,2,3-triazoles starting from allylic/benzylic alcohols. ![]() Investigations on the one-pot direct azidation of allylic/benzylic alcohols or their methyl ethers followed by the click reaction are reported.
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