Journal
CHEMISTRYSELECT
Volume 5, Issue 1, Pages 260-264Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/slct.201904688
Keywords
Azide; beta-Ketophosphonates; 1; 2; 3-Triazoles; Cycloaddition; Selectivity
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Funding
- Ministry of Education and Science of Ukraine [0118 U003610]
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The influence of base-solvent systems and substituents on the reaction of aryl azides with dimethyl 2-oxopropylphosphonate was studied. It was shown that azides with electron-withdrawing substituents in K2CO3/DMSO medium (mild conditions) afford 5-methyl-1-aryl-1H-1,2,3-triazole-4-ylphosphonates as major products. In contrast, azides with electron-donating substituents produce 1-aryl-5-methyl-1H-1,2,3-triazoles. Based on the obtained results the plausible mechanisms of the reactions were discussed and key points of selectivity control were indicated.
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