From [(11)C]CO(2) to [(11)C]amides: a rapid one-pot synthesis via the Mitsunobu reaction

A novel amide synthesis methodology is described using amines, CO(2) and Grignard reagents and Mitsunobu reagents. The method was applied to carbon-11 radiochemistry to label amides using cyclotron-produced [(11)C]CO(2). The synthetic utility of the one-pot labelling methodology was demonstrated by...

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Autores principales: Bongarzone, S., Runser, A., Taddei, C., Dheere, A. K. Haji, Gee, A. D.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2017
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5708528/
https://www.ncbi.nlm.nih.gov/pubmed/28447672
http://dx.doi.org/10.1039/c7cc01407d
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author Bongarzone, S.
Runser, A.
Taddei, C.
Dheere, A. K. Haji
Gee, A. D.
author_facet Bongarzone, S.
Runser, A.
Taddei, C.
Dheere, A. K. Haji
Gee, A. D.
author_sort Bongarzone, S.
collection PubMed
description A novel amide synthesis methodology is described using amines, CO(2) and Grignard reagents and Mitsunobu reagents. The method was applied to carbon-11 radiochemistry to label amides using cyclotron-produced [(11)C]CO(2). The synthetic utility of the one-pot labelling methodology was demonstrated by producing [(11)C]melatonin. The incorporation of [(11)C]CO(2) into [(11)C]melatonin was 36% – determined by radioHPLC 2 min post [(11)C]CO(2) delivery.
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spelling pubmed-57085282018-01-05 From [(11)C]CO(2) to [(11)C]amides: a rapid one-pot synthesis via the Mitsunobu reaction Bongarzone, S. Runser, A. Taddei, C. Dheere, A. K. Haji Gee, A. D. Chem Commun (Camb) Chemistry A novel amide synthesis methodology is described using amines, CO(2) and Grignard reagents and Mitsunobu reagents. The method was applied to carbon-11 radiochemistry to label amides using cyclotron-produced [(11)C]CO(2). The synthetic utility of the one-pot labelling methodology was demonstrated by producing [(11)C]melatonin. The incorporation of [(11)C]CO(2) into [(11)C]melatonin was 36% – determined by radioHPLC 2 min post [(11)C]CO(2) delivery. Royal Society of Chemistry 2017-05-11 2017-04-27 /pmc/articles/PMC5708528/ /pubmed/28447672 http://dx.doi.org/10.1039/c7cc01407d Text en This journal is © The Royal Society of Chemistry 2017 http://creativecommons.org/licenses/by/3.0/ This article is freely available. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence (CC BY 3.0)
spellingShingle Chemistry
Bongarzone, S.
Runser, A.
Taddei, C.
Dheere, A. K. Haji
Gee, A. D.
From [(11)C]CO(2) to [(11)C]amides: a rapid one-pot synthesis via the Mitsunobu reaction
title From [(11)C]CO(2) to [(11)C]amides: a rapid one-pot synthesis via the Mitsunobu reaction
title_full From [(11)C]CO(2) to [(11)C]amides: a rapid one-pot synthesis via the Mitsunobu reaction
title_fullStr From [(11)C]CO(2) to [(11)C]amides: a rapid one-pot synthesis via the Mitsunobu reaction
title_full_unstemmed From [(11)C]CO(2) to [(11)C]amides: a rapid one-pot synthesis via the Mitsunobu reaction
title_short From [(11)C]CO(2) to [(11)C]amides: a rapid one-pot synthesis via the Mitsunobu reaction
title_sort from [(11)c]co(2) to [(11)c]amides: a rapid one-pot synthesis via the mitsunobu reaction
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5708528/
https://www.ncbi.nlm.nih.gov/pubmed/28447672
http://dx.doi.org/10.1039/c7cc01407d
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