Mechanistic Pathways in Amide Activation: Flexible Synthesis of Oxazoles and Imidazoles

[Image: see text] The preparation of substituted aminooxazoles and aminoimidazoles from α-arylamides and α-aminoamides through triflic anhydride-mediated amide activation is reported. These reactions proceed via the intermediacy of nitrilium adducts and feature N-oxide-promoted umpolung of the α-pos...

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Autores principales: Di Mauro, Giovanni, Maryasin, Boris, Kaiser, Daniel, Shaaban, Saad, González, Leticia, Maulide, Nuno
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2017
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5525102/
https://www.ncbi.nlm.nih.gov/pubmed/28703599
http://dx.doi.org/10.1021/acs.orglett.7b01678
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author Di Mauro, Giovanni
Maryasin, Boris
Kaiser, Daniel
Shaaban, Saad
González, Leticia
Maulide, Nuno
author_facet Di Mauro, Giovanni
Maryasin, Boris
Kaiser, Daniel
Shaaban, Saad
González, Leticia
Maulide, Nuno
author_sort Di Mauro, Giovanni
collection PubMed
description [Image: see text] The preparation of substituted aminooxazoles and aminoimidazoles from α-arylamides and α-aminoamides through triflic anhydride-mediated amide activation is reported. These reactions proceed via the intermediacy of nitrilium adducts and feature N-oxide-promoted umpolung of the α-position of amides as well as a mechanistically intriguing sequence that results in sulfonyl migration from nitrogen to carbon. Quantum-chemical mechanistic analysis sheds light on the intricacies of the process.
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spelling pubmed-55251022017-08-03 Mechanistic Pathways in Amide Activation: Flexible Synthesis of Oxazoles and Imidazoles Di Mauro, Giovanni Maryasin, Boris Kaiser, Daniel Shaaban, Saad González, Leticia Maulide, Nuno Org Lett [Image: see text] The preparation of substituted aminooxazoles and aminoimidazoles from α-arylamides and α-aminoamides through triflic anhydride-mediated amide activation is reported. These reactions proceed via the intermediacy of nitrilium adducts and feature N-oxide-promoted umpolung of the α-position of amides as well as a mechanistically intriguing sequence that results in sulfonyl migration from nitrogen to carbon. Quantum-chemical mechanistic analysis sheds light on the intricacies of the process. American Chemical Society 2017-07-13 2017-07-21 /pmc/articles/PMC5525102/ /pubmed/28703599 http://dx.doi.org/10.1021/acs.orglett.7b01678 Text en Copyright © 2017 American Chemical Society This is an open access article published under a Creative Commons Attribution (CC-BY) License (http://pubs.acs.org/page/policy/authorchoice_ccby_termsofuse.html) , which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.
spellingShingle Di Mauro, Giovanni
Maryasin, Boris
Kaiser, Daniel
Shaaban, Saad
González, Leticia
Maulide, Nuno
Mechanistic Pathways in Amide Activation: Flexible Synthesis of Oxazoles and Imidazoles
title Mechanistic Pathways in Amide Activation: Flexible Synthesis of Oxazoles and Imidazoles
title_full Mechanistic Pathways in Amide Activation: Flexible Synthesis of Oxazoles and Imidazoles
title_fullStr Mechanistic Pathways in Amide Activation: Flexible Synthesis of Oxazoles and Imidazoles
title_full_unstemmed Mechanistic Pathways in Amide Activation: Flexible Synthesis of Oxazoles and Imidazoles
title_short Mechanistic Pathways in Amide Activation: Flexible Synthesis of Oxazoles and Imidazoles
title_sort mechanistic pathways in amide activation: flexible synthesis of oxazoles and imidazoles
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5525102/
https://www.ncbi.nlm.nih.gov/pubmed/28703599
http://dx.doi.org/10.1021/acs.orglett.7b01678
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