Development of Synthetic Chemistry on Organic Azides by Brearing their 1,3-Dipolar Characteristics

Abstract

Organic azides are well-known for the synthetic organic reactions by their energetic characteristics and the click functionality connecting two components. Especially in click chemistry, the azido groups as 1,3-dipolar play a key role in chemical biology. On the other hand, azido groups can also work as nucleophiles possessing diazonium leaving groups and as electrophiles, but the low 1,3-dipolar reactivity use has of avoided organic azides. their use. As Herein, nucleophiles, we disclose the organic our synthetic azides with achievements allyl／propargyl in the cations non- and sulfonium ions gave the appropriate products, including C-C bond migration. We also demonstrated that the intramolecular hydrogen bonding interaction promoted the electrophilicity and suppressed the nucleophilicity of the azides to achieve site-selective conjugation. Furthermore, β - elimination followed by condensation converted the azido groups at the carbonyl α -position to the different click functional groups. This site-selective azido group conversion enabled the undistinguishable triazide molecule to the distinguishable triple-click scaffold compound possessing three different click groups.