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Exploiting the Nucleophilicity of NH Imines: Synthesis of Enamides from Alkyl Azides and Acid Anhydrides
Author(s) -
Han Junghoon,
Jeon Mina,
Pak Han Kyu,
Rhee Young Ho,
Park Jaiwook
Publication year - 2014
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201400584
Subject(s) - chemistry , triethylamine , nucleophile , isomerization , alkyl , organic chemistry , acetic anhydride , acetic acid , carboxylic acid , catalysis , medicinal chemistry
The nucleophilicity of N ‐unsubstituted imines, which were generated from alkyl azides by a ruthenium‐catalyzed reaction, was investigated in the reaction with acid anhydrides. The initial products were N ‐acylimines, which isomerized to the corresponding enamides. Heating or triethylamine facilitated the isomerization of N ‐acylimines that are stable at room temperature. A wide range of acyclic and cyclic enamides containing various functional groups was successfully synthesized under mild conditions. In addition to acetic anhydride, various acid anhydrides were applicable. From the reaction with cyclic anhydrides, enamides containing carboxylic acid group were obtained.