Synthesis of 7-Aminocoumarins from 7-Hydroxycoumarins via Amide Smiles Rearrangement

[Image: see text] N-Substituted 7-aminocoumarins can be synthesized from readily available 7-hydroxycoumarins via alkylation with α-bromoacetamides and subsequent tandem O → N Smiles rearrangement–amide hydrolysis. The key rearrangement sequence proceeds under mild conditions to provide convenient a...

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Autores principales: Lippe, Daniel S., Elghawy, Omar, Zucker, Adam M., Yanagawa, Evan S. K., Mathews, Erin, Ahmed, Yusef G., D’Elia, Paige N., Bimson, Sabrina, Walvoord, Ryan R.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9535735/
https://www.ncbi.nlm.nih.gov/pubmed/36211046
http://dx.doi.org/10.1021/acsomega.2c04653
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author Lippe, Daniel S.
Elghawy, Omar
Zucker, Adam M.
Yanagawa, Evan S. K.
Mathews, Erin
Ahmed, Yusef G.
D’Elia, Paige N.
Bimson, Sabrina
Walvoord, Ryan R.
author_facet Lippe, Daniel S.
Elghawy, Omar
Zucker, Adam M.
Yanagawa, Evan S. K.
Mathews, Erin
Ahmed, Yusef G.
D’Elia, Paige N.
Bimson, Sabrina
Walvoord, Ryan R.
author_sort Lippe, Daniel S.
collection PubMed
description [Image: see text] N-Substituted 7-aminocoumarins can be synthesized from readily available 7-hydroxycoumarins via alkylation with α-bromoacetamides and subsequent tandem O → N Smiles rearrangement–amide hydrolysis. The key rearrangement sequence proceeds under mild conditions to provide convenient access to various N-alkyl and N-aryl products in moderate to high yields. The process is operationally simple, inexpensive, transition-metal-free, and can be telescoped into a one-pot process.
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spelling pubmed-95357352022-10-07 Synthesis of 7-Aminocoumarins from 7-Hydroxycoumarins via Amide Smiles Rearrangement Lippe, Daniel S. Elghawy, Omar Zucker, Adam M. Yanagawa, Evan S. K. Mathews, Erin Ahmed, Yusef G. D’Elia, Paige N. Bimson, Sabrina Walvoord, Ryan R. ACS Omega [Image: see text] N-Substituted 7-aminocoumarins can be synthesized from readily available 7-hydroxycoumarins via alkylation with α-bromoacetamides and subsequent tandem O → N Smiles rearrangement–amide hydrolysis. The key rearrangement sequence proceeds under mild conditions to provide convenient access to various N-alkyl and N-aryl products in moderate to high yields. The process is operationally simple, inexpensive, transition-metal-free, and can be telescoped into a one-pot process. American Chemical Society 2022-09-21 /pmc/articles/PMC9535735/ /pubmed/36211046 http://dx.doi.org/10.1021/acsomega.2c04653 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/).
spellingShingle Lippe, Daniel S.
Elghawy, Omar
Zucker, Adam M.
Yanagawa, Evan S. K.
Mathews, Erin
Ahmed, Yusef G.
D’Elia, Paige N.
Bimson, Sabrina
Walvoord, Ryan R.
Synthesis of 7-Aminocoumarins from 7-Hydroxycoumarins via Amide Smiles Rearrangement
title Synthesis of 7-Aminocoumarins from 7-Hydroxycoumarins via Amide Smiles Rearrangement
title_full Synthesis of 7-Aminocoumarins from 7-Hydroxycoumarins via Amide Smiles Rearrangement
title_fullStr Synthesis of 7-Aminocoumarins from 7-Hydroxycoumarins via Amide Smiles Rearrangement
title_full_unstemmed Synthesis of 7-Aminocoumarins from 7-Hydroxycoumarins via Amide Smiles Rearrangement
title_short Synthesis of 7-Aminocoumarins from 7-Hydroxycoumarins via Amide Smiles Rearrangement
title_sort synthesis of 7-aminocoumarins from 7-hydroxycoumarins via amide smiles rearrangement
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9535735/
https://www.ncbi.nlm.nih.gov/pubmed/36211046
http://dx.doi.org/10.1021/acsomega.2c04653
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