Regioselective (thio)carbamoylation of 2,7-di-tert-butylpyrene at the 1-position with iso(thio)cyanates

It has been found that 2,7-di-tert-butylpyrene reacts with aliphatic iso(thio)cyanates in the presence of trifluoromethanesulfonic acid to exclusively afford the corresponding 1-substituted (thio)amides in high yields. For aromatic iso(thio)cyanates the reaction is less regioselective, although subs...

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Autores principales: Wrona-Piotrowicz, Anna, Witalewska, Marzena, Zakrzewski, Janusz, Makal, Anna
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2017
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5480332/
https://www.ncbi.nlm.nih.gov/pubmed/28684982
http://dx.doi.org/10.3762/bjoc.13.102
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author Wrona-Piotrowicz, Anna
Witalewska, Marzena
Zakrzewski, Janusz
Makal, Anna
author_facet Wrona-Piotrowicz, Anna
Witalewska, Marzena
Zakrzewski, Janusz
Makal, Anna
author_sort Wrona-Piotrowicz, Anna
collection PubMed
description It has been found that 2,7-di-tert-butylpyrene reacts with aliphatic iso(thio)cyanates in the presence of trifluoromethanesulfonic acid to exclusively afford the corresponding 1-substituted (thio)amides in high yields. For aromatic iso(thio)cyanates the reaction is less regioselective, although substitution at the 1-position prevails. For ethoxycarbonyl isothiocyanate, apart from the 1-substituted thioamide, 1,8-disubstituted thioamide and 2,7-di-tert-butylpyrene-1-carbonitrile are formed (especially at longer reaction times).
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spelling pubmed-54803322017-07-06 Regioselective (thio)carbamoylation of 2,7-di-tert-butylpyrene at the 1-position with iso(thio)cyanates Wrona-Piotrowicz, Anna Witalewska, Marzena Zakrzewski, Janusz Makal, Anna Beilstein J Org Chem Full Research Paper It has been found that 2,7-di-tert-butylpyrene reacts with aliphatic iso(thio)cyanates in the presence of trifluoromethanesulfonic acid to exclusively afford the corresponding 1-substituted (thio)amides in high yields. For aromatic iso(thio)cyanates the reaction is less regioselective, although substitution at the 1-position prevails. For ethoxycarbonyl isothiocyanate, apart from the 1-substituted thioamide, 1,8-disubstituted thioamide and 2,7-di-tert-butylpyrene-1-carbonitrile are formed (especially at longer reaction times). Beilstein-Institut 2017-05-29 /pmc/articles/PMC5480332/ /pubmed/28684982 http://dx.doi.org/10.3762/bjoc.13.102 Text en Copyright © 2017, Wrona-Piotrowicz 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), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. 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
Wrona-Piotrowicz, Anna
Witalewska, Marzena
Zakrzewski, Janusz
Makal, Anna
Regioselective (thio)carbamoylation of 2,7-di-tert-butylpyrene at the 1-position with iso(thio)cyanates
title Regioselective (thio)carbamoylation of 2,7-di-tert-butylpyrene at the 1-position with iso(thio)cyanates
title_full Regioselective (thio)carbamoylation of 2,7-di-tert-butylpyrene at the 1-position with iso(thio)cyanates
title_fullStr Regioselective (thio)carbamoylation of 2,7-di-tert-butylpyrene at the 1-position with iso(thio)cyanates
title_full_unstemmed Regioselective (thio)carbamoylation of 2,7-di-tert-butylpyrene at the 1-position with iso(thio)cyanates
title_short Regioselective (thio)carbamoylation of 2,7-di-tert-butylpyrene at the 1-position with iso(thio)cyanates
title_sort regioselective (thio)carbamoylation of 2,7-di-tert-butylpyrene at the 1-position with iso(thio)cyanates
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5480332/
https://www.ncbi.nlm.nih.gov/pubmed/28684982
http://dx.doi.org/10.3762/bjoc.13.102
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