TY - JOUR
T1 - Formation of 2-Imino Benzo[e]-1,3-oxazin-4-ones from Reactions of Salicylic Acids and Anilines with HATU
T2 - Mechanistic and Synthetic Studies
AU - Leas, Derek A.
AU - Wu, Jianbo
AU - Ezell, Edward L.
AU - Garrison, Jered C.
AU - Vennerstrom, Jonathan L.
AU - Dong, Yuxiang
N1 - Publisher Copyright:
© 2018 American Chemical Society.
PY - 2018/1/31
Y1 - 2018/1/31
N2 - We describe a new 1-[Bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (HATU)-mediated coupling reaction to produce 2-imino benzo[e]-1,3-oxazin-4-ones from salicylic acids and anilines. Mechanistic studies support a reaction pathway in which HATU mediates carbon transfer to the initially formed salicylanilides to form in succession reactive tetramethylisouronium and N-acyl(dimethyl)isouronium intermediates, which then undergo imine-iminium exchange to generate the desired oxazinones.
AB - We describe a new 1-[Bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (HATU)-mediated coupling reaction to produce 2-imino benzo[e]-1,3-oxazin-4-ones from salicylic acids and anilines. Mechanistic studies support a reaction pathway in which HATU mediates carbon transfer to the initially formed salicylanilides to form in succession reactive tetramethylisouronium and N-acyl(dimethyl)isouronium intermediates, which then undergo imine-iminium exchange to generate the desired oxazinones.
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U2 - 10.1021/acsomega.7b01824
DO - 10.1021/acsomega.7b01824
M3 - Article
C2 - 29399653
AN - SCOPUS:85054415724
SN - 2470-1343
VL - 3
SP - 781
EP - 787
JO - ACS Omega
JF - ACS Omega
IS - 1
ER -