Influence of Steric Effect on the Pseudo-Multicomponent Synthesis of N-Aroylmethyl-4-Arylimidazoles

A pseudo-three-component synthesis of N-aroylmethylimidazoles 3 with three new C–N bonds formed regioselectively under microwave conditions was developed. Products were obtained by reacting two equivalents of aroylmethyl bromide (ArCOCH(2)Br, 1) with the appropriate amidine salt (RCN(2)H(3).HX, 2) a...

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Autores principales: Elejalde-Cadena, Nerith Rocio, García-Olave, Mayra, Figueroa, David, Vidossich, Pietro, Miscione, Gian Pietro, Portilla, Jaime
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8874432/
https://www.ncbi.nlm.nih.gov/pubmed/35208948
http://dx.doi.org/10.3390/molecules27041165
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author Elejalde-Cadena, Nerith Rocio
García-Olave, Mayra
Figueroa, David
Vidossich, Pietro
Miscione, Gian Pietro
Portilla, Jaime
author_facet Elejalde-Cadena, Nerith Rocio
García-Olave, Mayra
Figueroa, David
Vidossich, Pietro
Miscione, Gian Pietro
Portilla, Jaime
author_sort Elejalde-Cadena, Nerith Rocio
collection PubMed
description A pseudo-three-component synthesis of N-aroylmethylimidazoles 3 with three new C–N bonds formed regioselectively under microwave conditions was developed. Products were obtained by reacting two equivalents of aroylmethyl bromide (ArCOCH(2)Br, 1) with the appropriate amidine salt (RCN(2)H(3).HX, 2) and with K(2)CO(3) as a base in acetonitrile. The bicomponent reaction also occurred, giving the expected 4(5)-aryl-1H-imidazoles 4. Notably, the ratio of products 3 and 4 is governed by steric factors of the amidine 2 (i.e., R = H, CH(3), Ph). Therefore, a computational study was carried out to understand the reaction course regarding product ratio (3/4), regioselectivity, and the steric effects of the amidine substituent group.
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spelling pubmed-88744322022-02-26 Influence of Steric Effect on the Pseudo-Multicomponent Synthesis of N-Aroylmethyl-4-Arylimidazoles Elejalde-Cadena, Nerith Rocio García-Olave, Mayra Figueroa, David Vidossich, Pietro Miscione, Gian Pietro Portilla, Jaime Molecules Article A pseudo-three-component synthesis of N-aroylmethylimidazoles 3 with three new C–N bonds formed regioselectively under microwave conditions was developed. Products were obtained by reacting two equivalents of aroylmethyl bromide (ArCOCH(2)Br, 1) with the appropriate amidine salt (RCN(2)H(3).HX, 2) and with K(2)CO(3) as a base in acetonitrile. The bicomponent reaction also occurred, giving the expected 4(5)-aryl-1H-imidazoles 4. Notably, the ratio of products 3 and 4 is governed by steric factors of the amidine 2 (i.e., R = H, CH(3), Ph). Therefore, a computational study was carried out to understand the reaction course regarding product ratio (3/4), regioselectivity, and the steric effects of the amidine substituent group. MDPI 2022-02-09 /pmc/articles/PMC8874432/ /pubmed/35208948 http://dx.doi.org/10.3390/molecules27041165 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Elejalde-Cadena, Nerith Rocio
García-Olave, Mayra
Figueroa, David
Vidossich, Pietro
Miscione, Gian Pietro
Portilla, Jaime
Influence of Steric Effect on the Pseudo-Multicomponent Synthesis of N-Aroylmethyl-4-Arylimidazoles
title Influence of Steric Effect on the Pseudo-Multicomponent Synthesis of N-Aroylmethyl-4-Arylimidazoles
title_full Influence of Steric Effect on the Pseudo-Multicomponent Synthesis of N-Aroylmethyl-4-Arylimidazoles
title_fullStr Influence of Steric Effect on the Pseudo-Multicomponent Synthesis of N-Aroylmethyl-4-Arylimidazoles
title_full_unstemmed Influence of Steric Effect on the Pseudo-Multicomponent Synthesis of N-Aroylmethyl-4-Arylimidazoles
title_short Influence of Steric Effect on the Pseudo-Multicomponent Synthesis of N-Aroylmethyl-4-Arylimidazoles
title_sort influence of steric effect on the pseudo-multicomponent synthesis of n-aroylmethyl-4-arylimidazoles
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8874432/
https://www.ncbi.nlm.nih.gov/pubmed/35208948
http://dx.doi.org/10.3390/molecules27041165
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