Indium(III) triflate catalyzed tandem azidation/1,3-dipolar cycloaddition reaction of ω,ω-dialkoxyalkyne derivatives with trimethylsilyl azide |
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Authors: | Hikaru Yanai |
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Institution: | School of Pharmacy, Tokyo University of Pharmacy and Life Science, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan |
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Abstract: | The azidation reaction of dialkyl acetal derivatives with trimethylsilyl azide (TMSN3) was efficiently catalyzed by 1-5 mol % of In(OTf)3. The major product differed depending on the substrate structure and molar ratio of TMSN3, that is, aliphatic acetals provided α-azido ether derivatives, while aromatic acetal (benzaldehyde dimethyl acetal) provided gem-diazide, respectively. Furthermore, novel tandem azidation/1,3-dipolar cycloaddition reaction using alkynyl acetal derivatives gave bicyclic triazolo-heterocyclic compounds, recognized as chemically modified aza-sugar analogues, in high yields under mild conditions. |
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Keywords: | Indium(III) triflate Azidation 1 3-Dipolar cycloaddition Tandem reaction Triazolo-heterocyclic compounds |
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