Reaction of Amide and Sodium Azide for the Synthesis of Acyl Azide, Urea, and Iminophosphorane
Devaneyan Joseph, Sunwoo Lee
Abstract
Amides reacted with NaN3 to give the acyl azides in DMF at 25 °C and produce the symmetrical ureas in THF/H2O at 80 °C via the sequential reaction of acyl substitution and Curtius rearrangement. All acyl azides were also obtained from the secondary amides via sequential reaction of p-toluenesulfonyl chloride and NaN3. In addition, keto-stabilized iminophosphoranes were prepared from a one-pot reaction of amides, NaN3, and phosphines.
Topics & Concepts
ChemistrySodium azideAmideAzideCurtius rearrangementAcyl chlorideUreaNucleophilic acyl substitutionSodiumOrganic chemistryAcylationMedicinal chemistryChlorideCatalysisChemical Synthesis and AnalysisSynthetic Organic Chemistry MethodsSynthesis and Catalytic Reactions