Reaction of Amide and Sodium Azide for the Synthesis of Acyl Azide, Urea, and Iminophosphorane

Devaneyan Joseph; Sunwoo Lee

doi:10.1021/acs.orglett.2c02429

Reaction of Amide and Sodium Azide for the Synthesis of Acyl Azide, Urea, and Iminophosphorane

Org Lett. 2022 Aug 26;24(33):6186-6191. doi: 10.1021/acs.orglett.2c02429. Epub 2022 Aug 12.

Authors

Devaneyan Joseph¹, Sunwoo Lee¹

Affiliation

¹ Department of Chemistry, Chonnam National University, Gwangju, 61186, Republic of Korea.

PMID: 35959978
DOI: 10.1021/acs.orglett.2c02429

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.