Preparation of Polyfunctionalized Aromatic Nitriles from Aryl Oxazolines

A selective ortho,ortho’‐functionalization of readily available aryl oxazolines by two successive magnesiations with sBu(2)Mg in toluene followed by trapping reactions with electrophiles, such as (hetero)aryl iodides or bromides, iodine, tosyl cyanide, ethyl cyanoformate or allylic bromides (39 exam...

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Autores principales: Hess, A., Guelen, H. C., Alandini, N., Mourati, A., Guersoy, Y. C., Knochel, P.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2021
Materias:
Research Articles
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9300023/
https://www.ncbi.nlm.nih.gov/pubmed/34766655
http://dx.doi.org/10.1002/chem.202103700
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author Hess, A.
Guelen, H. C.
Alandini, N.
Mourati, A.
Guersoy, Y. C.
Knochel, P.
author_facet Hess, A.
Guelen, H. C.
Alandini, N.
Mourati, A.
Guersoy, Y. C.
Knochel, P.
author_sort Hess, A.
collection PubMed
description A selective ortho,ortho’‐functionalization of readily available aryl oxazolines by two successive magnesiations with sBu(2)Mg in toluene followed by trapping reactions with electrophiles, such as (hetero)aryl iodides or bromides, iodine, tosyl cyanide, ethyl cyanoformate or allylic bromides (39 examples, 62–99 % yield) is reported. Treatment of these aryl oxazolines with excess oxalyl chloride and catalytic amounts of DMF (50 °C, 4 h) provided the corresponding nitriles (36 examples, 73–99 % yield). Conversions of these nitriles to valuable heterocycles are reported, and a tentative mechanism is proposed.
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spelling pubmed-93000232022-07-21 Preparation of Polyfunctionalized Aromatic Nitriles from Aryl Oxazolines Hess, A. Guelen, H. C. Alandini, N. Mourati, A. Guersoy, Y. C. Knochel, P. Chemistry Research Articles A selective ortho,ortho’‐functionalization of readily available aryl oxazolines by two successive magnesiations with sBu(2)Mg in toluene followed by trapping reactions with electrophiles, such as (hetero)aryl iodides or bromides, iodine, tosyl cyanide, ethyl cyanoformate or allylic bromides (39 examples, 62–99 % yield) is reported. Treatment of these aryl oxazolines with excess oxalyl chloride and catalytic amounts of DMF (50 °C, 4 h) provided the corresponding nitriles (36 examples, 73–99 % yield). Conversions of these nitriles to valuable heterocycles are reported, and a tentative mechanism is proposed. John Wiley and Sons Inc. 2021-12-02 2022-01-03 /pmc/articles/PMC9300023/ /pubmed/34766655 http://dx.doi.org/10.1002/chem.202103700 Text en © 2021 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH https://creativecommons.org/licenses/by-nc-nd/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc-nd/4.0/ (https://creativecommons.org/licenses/by-nc-nd/4.0/) License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made.
spellingShingle Research Articles
Hess, A.
Guelen, H. C.
Alandini, N.
Mourati, A.
Guersoy, Y. C.
Knochel, P.
Preparation of Polyfunctionalized Aromatic Nitriles from Aryl Oxazolines
title Preparation of Polyfunctionalized Aromatic Nitriles from Aryl Oxazolines
title_full Preparation of Polyfunctionalized Aromatic Nitriles from Aryl Oxazolines
title_fullStr Preparation of Polyfunctionalized Aromatic Nitriles from Aryl Oxazolines
title_full_unstemmed Preparation of Polyfunctionalized Aromatic Nitriles from Aryl Oxazolines
title_short Preparation of Polyfunctionalized Aromatic Nitriles from Aryl Oxazolines
title_sort preparation of polyfunctionalized aromatic nitriles from aryl oxazolines
topic Research Articles
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9300023/
https://www.ncbi.nlm.nih.gov/pubmed/34766655
http://dx.doi.org/10.1002/chem.202103700
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