Azides are nitrogen-containing compounds that have a variety of applications in chemical synthesis. Azides can act as nucleophiles, ligands, precursors, and reagents for different types of reactions. In this paragraph, we will briefly describe some of the uses of azides as reagents for chemical synthesis.
One of the use of azides is as nucleophiles for substitution and addition reactions. Azides can react with alkyl halides or epoxides to form alkyl or alkoxy azides via SN2 mechanism . These products can then be reduced to primary amines by hydrogenation or Staudinger reaction. Azides can also undergo 1,3-dipolar cycloaddition with alkynes to form 1,2,3-triazoles in a highly selective and efficient manner. This reaction is known as the click chemistry and has wide applications in bioconjugation and drug discovery.
A secound use of azides is as precursors for other functional groups. Azides can be converted to isocyanates by Curtius rearrangement or Schmidt reaction. Isocyanates can then react with alcohols or amines to form urethanes or ureas respectively. Azides can also be transformed into nitrenes by photolysis or thermolysis. Nitrenes are highly reactive intermediates that can insert into C-H bonds, cyclize to form heterocycles, or dimerize to form azo compounds.
In summary, azides are versatile reagents for chemical synthesis that can provide nucleophilic attack, cycloaddition reaction, and functional group transformation.
