Recent Advances in Reactions of Azides

Abstract

Azides are important intermediates in organic synthesis. They can function as precursors to form amines, amides, quinolones, pyridines, triazoles, amidines, indoles, and so on. Although there are some reviews about the applications of azides, few are concerned about their fundamental mechanisms. This review will focus on recent advances of azides based on three reactivity patterns, which may enlighten the further research.

Recyclable Organocatalyst for One‐Pot Asymmetric Synthesis of Dihydrofuranone and Tetrahydropyranone Spirooxindoles

“…The formation of intramolecular H-bond could stabilize cyclic hemiketals 6 to prevent the dehydration. Stabilization of cyclic hemiketals through intramolecular H-bond has been observed from our previous work [12] and also reported in the literature. [13] The recovery of fluorous catalyst from a one-gram scale reaction of 2a was carried out by using 100 mg of cat-1 (Scheme 5).…”

Synthesis, Stability and Reactivity of α‐Fluorinated Azidoalkanes

“…Thermal and photo-induced decomposition gives highlyr eactive nitrenes. [1][2][3] However,s mall organic azides are often unstablea nd can decompose explosively.T his concern was probably the reason why C1 fluorinated azidess uch as azidotrifluoromethane or azidodifluoromethane, although they have been known since the 1960s and 1970s, have not been investigated systematicallyf or synthetic purposes.T he situation is now changing. Many highly fluorinated azides are stable compounds and undergo av ariety of usefult ransformations.…”

Copper‐Catalyzed Synthesis of 3‐NO2 Quinolines from o‐Azidobenzaldehyde and Nitro‐olefins and its Application in the Concise Synthesis of Quindolines

“…Another possibility is that the reaction proceeds via a nitrene thermolysis mechanism. The nitrene could be trapped by 2 a directly or further formed benzisoxazole ( 6 ) intermediate to give 4 a , meanwhile it also could be converted to 5 by hydrogen abstraction . However, directly heating of 1 a in DMF or neat reaction condition, 6 was not observed in 2 h (Scheme d).…”