Formation of 2-Imino Benzo[e]-1,3-oxazin-4-ones from Reactions of Salicylic Acids and Anilines with HATU: Mechanistic and Synthetic Studies

[Image: see text] 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 whic...

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Autores principales: Leas, Derek A., Wu, Jianbo, Ezell, Edward L., Garrison, Jered C., Vennerstrom, Jonathan L., Dong, Yuxiang
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2018
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5793036/
https://www.ncbi.nlm.nih.gov/pubmed/29399653
http://dx.doi.org/10.1021/acsomega.7b01824
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author Leas, Derek A.
Wu, Jianbo
Ezell, Edward L.
Garrison, Jered C.
Vennerstrom, Jonathan L.
Dong, Yuxiang
author_facet Leas, Derek A.
Wu, Jianbo
Ezell, Edward L.
Garrison, Jered C.
Vennerstrom, Jonathan L.
Dong, Yuxiang
author_sort Leas, Derek A.
collection PubMed
description [Image: see text] 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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spelling pubmed-57930362018-02-02 Formation of 2-Imino Benzo[e]-1,3-oxazin-4-ones from Reactions of Salicylic Acids and Anilines with HATU: Mechanistic and Synthetic Studies Leas, Derek A. Wu, Jianbo Ezell, Edward L. Garrison, Jered C. Vennerstrom, Jonathan L. Dong, Yuxiang ACS Omega [Image: see text] 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. American Chemical Society 2018-01-22 /pmc/articles/PMC5793036/ /pubmed/29399653 http://dx.doi.org/10.1021/acsomega.7b01824 Text en Copyright © 2018 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Leas, Derek A.
Wu, Jianbo
Ezell, Edward L.
Garrison, Jered C.
Vennerstrom, Jonathan L.
Dong, Yuxiang
Formation of 2-Imino Benzo[e]-1,3-oxazin-4-ones from Reactions of Salicylic Acids and Anilines with HATU: Mechanistic and Synthetic Studies
title Formation of 2-Imino Benzo[e]-1,3-oxazin-4-ones from Reactions of Salicylic Acids and Anilines with HATU: Mechanistic and Synthetic Studies
title_full Formation of 2-Imino Benzo[e]-1,3-oxazin-4-ones from Reactions of Salicylic Acids and Anilines with HATU: Mechanistic and Synthetic Studies
title_fullStr Formation of 2-Imino Benzo[e]-1,3-oxazin-4-ones from Reactions of Salicylic Acids and Anilines with HATU: Mechanistic and Synthetic Studies
title_full_unstemmed Formation of 2-Imino Benzo[e]-1,3-oxazin-4-ones from Reactions of Salicylic Acids and Anilines with HATU: Mechanistic and Synthetic Studies
title_short Formation of 2-Imino Benzo[e]-1,3-oxazin-4-ones from Reactions of Salicylic Acids and Anilines with HATU: Mechanistic and Synthetic Studies
title_sort formation of 2-imino benzo[e]-1,3-oxazin-4-ones from reactions of salicylic acids and anilines with hatu: mechanistic and synthetic studies
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5793036/
https://www.ncbi.nlm.nih.gov/pubmed/29399653
http://dx.doi.org/10.1021/acsomega.7b01824
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