Hydroazidation of phenacylideneoxindoles: Synthesis of 3-substituted 3-azido-1,3-dihydro-2H-indol-2-ones via anti-electron addition

A simple synthetic strategy of 3-substituted 3-azido-1,3-dihydro-2H-indol-2-ones was realized through hydroazidation of phenacylideneoxindoles with azidotrimethylsilane under mild conditions. In the pres-ence of tetrabutylammonium fluoride, the reaction proceeds by the anti-electron addition of N3. This azi-dation method of phenacylideneoxindoles is valuable in pharmaceutical synthesis and chemical biology studies because of its mild reaction conditions and simple purification of products without contamination by any transition-metal residues.(c) 2023 Elsevier Ltd. All rights reserved.

Automated summary

A simple synthetic strategy for 3-substituted 3-azido-1,3-dihydro-2H-indol-2-ones was achieved through hydroazidation of phenacylideneoxindoles with azidotrimethylsilane under mild conditions. The reaction proceeds by the anti-electron addition of N3 in the presence of tetrabutylammonium fluoride. This azi-dation method of phenacylideneoxindoles is valuable in pharmaceutical synthesis and chemical biology studies due to its mild reaction conditions and simple purification of products without contamination by any transition-metal residues.