Regiodivergent synthesis of functionalized pyrimidines and imidazoles through phenacyl azides in deep eutectic solvents

We report that phenacyl azides are key compounds for a regiodivergent synthesis of valuable, functionalized imidazole (32–98% yield) and pyrimidine derivatives (45–88% yield), with a broad substrate scope, when using deep eutectic solvents [choline chloride (ChCl)/glycerol (1:2 mol/mol) and ChCl/ure...

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Autores principales: Vitale, Paola, Cicco, Luciana, Cellamare, Ilaria, Perna, Filippo M, Salomone, Antonio, Capriati, Vito
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2020
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7418094/
https://www.ncbi.nlm.nih.gov/pubmed/32802208
http://dx.doi.org/10.3762/bjoc.16.158
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author Vitale, Paola
Cicco, Luciana
Cellamare, Ilaria
Perna, Filippo M
Salomone, Antonio
Capriati, Vito
author_facet Vitale, Paola
Cicco, Luciana
Cellamare, Ilaria
Perna, Filippo M
Salomone, Antonio
Capriati, Vito
author_sort Vitale, Paola
collection PubMed
description We report that phenacyl azides are key compounds for a regiodivergent synthesis of valuable, functionalized imidazole (32–98% yield) and pyrimidine derivatives (45–88% yield), with a broad substrate scope, when using deep eutectic solvents [choline chloride (ChCl)/glycerol (1:2 mol/mol) and ChCl/urea (1:2 mol/mol)] as environmentally benign and non-innocent reaction media, by modulating the temperature (25 or 80 °C) in the presence or absence of bases (Et(3)N).
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spelling pubmed-74180942020-08-13 Regiodivergent synthesis of functionalized pyrimidines and imidazoles through phenacyl azides in deep eutectic solvents Vitale, Paola Cicco, Luciana Cellamare, Ilaria Perna, Filippo M Salomone, Antonio Capriati, Vito Beilstein J Org Chem Full Research Paper We report that phenacyl azides are key compounds for a regiodivergent synthesis of valuable, functionalized imidazole (32–98% yield) and pyrimidine derivatives (45–88% yield), with a broad substrate scope, when using deep eutectic solvents [choline chloride (ChCl)/glycerol (1:2 mol/mol) and ChCl/urea (1:2 mol/mol)] as environmentally benign and non-innocent reaction media, by modulating the temperature (25 or 80 °C) in the presence or absence of bases (Et(3)N). Beilstein-Institut 2020-08-05 /pmc/articles/PMC7418094/ /pubmed/32802208 http://dx.doi.org/10.3762/bjoc.16.158 Text en Copyright © 2020, Vitale et al. https://creativecommons.org/licenses/by/4.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0). Please note that the reuse, redistribution and reproduction in particular requires that the authors and source are credited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Vitale, Paola
Cicco, Luciana
Cellamare, Ilaria
Perna, Filippo M
Salomone, Antonio
Capriati, Vito
Regiodivergent synthesis of functionalized pyrimidines and imidazoles through phenacyl azides in deep eutectic solvents
title Regiodivergent synthesis of functionalized pyrimidines and imidazoles through phenacyl azides in deep eutectic solvents
title_full Regiodivergent synthesis of functionalized pyrimidines and imidazoles through phenacyl azides in deep eutectic solvents
title_fullStr Regiodivergent synthesis of functionalized pyrimidines and imidazoles through phenacyl azides in deep eutectic solvents
title_full_unstemmed Regiodivergent synthesis of functionalized pyrimidines and imidazoles through phenacyl azides in deep eutectic solvents
title_short Regiodivergent synthesis of functionalized pyrimidines and imidazoles through phenacyl azides in deep eutectic solvents
title_sort regiodivergent synthesis of functionalized pyrimidines and imidazoles through phenacyl azides in deep eutectic solvents
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7418094/
https://www.ncbi.nlm.nih.gov/pubmed/32802208
http://dx.doi.org/10.3762/bjoc.16.158
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