Reaction of Some Substituted (Un)Substituted Isatins with 1,ω-Alkanes and Their Products with Sodium Azide

Abstract

Azide derivatives of isatins were the initial materials needed for click chemistry, so as to form 1,2,3-triazoles in order to synthesize the hybrid compounds of 1,2,3-triazole–isatin with monosaccharide moieties. The required substituted isatins were prepared according to the Sandmeyer method from corresponding substituted anilines. N-(ω-bromoalkyl) isatins were prepared through the nucleophilic reaction, SN2, of (un)substituted isatins with appropriate dibromoalkanes. Some ω-azidoalkylisatins were synthesized by the reaction of corresponding ω-bromoalkylisatins with sodium azide. The reactions were performed in dry DMF as solvents in the presence of K2CO3 as the base and KI as the promoting agent. The product yields reached 30–85%.

Keywords

• azide
• alkylation
• azidation dibromoalkanes
• isatins