The unexpected influence of aryl substituents in N-aryl-3-oxobutanamides on the behavior of their multicomponent reactions with 5-amino-3-methylisoxazole and salicylaldehyde

The switchable three-component reactions of 5-amino-3-methylisoxazole, salicylaldehyde and N-aryl-3-oxobutanamides under different conditions were studied and discussed. The unexpected influence of the aryl substituent in N-aryl-3-oxobutanamides on the behavior of the reaction was discovered. The ke...

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Autores principales: Tkachenko, Volodymyr V, Muravyova, Elena A, Desenko, Sergey M, Shishkin, Oleg V, Shishkina, Svetlana V, Sysoiev, Dmytro O, Müller, Thomas J J, Chebanov, Valentin A
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2014
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4311697/
https://www.ncbi.nlm.nih.gov/pubmed/25670972
http://dx.doi.org/10.3762/bjoc.10.320
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author Tkachenko, Volodymyr V
Muravyova, Elena A
Desenko, Sergey M
Shishkin, Oleg V
Shishkina, Svetlana V
Sysoiev, Dmytro O
Müller, Thomas J J
Chebanov, Valentin A
author_facet Tkachenko, Volodymyr V
Muravyova, Elena A
Desenko, Sergey M
Shishkin, Oleg V
Shishkina, Svetlana V
Sysoiev, Dmytro O
Müller, Thomas J J
Chebanov, Valentin A
author_sort Tkachenko, Volodymyr V
collection PubMed
description The switchable three-component reactions of 5-amino-3-methylisoxazole, salicylaldehyde and N-aryl-3-oxobutanamides under different conditions were studied and discussed. The unexpected influence of the aryl substituent in N-aryl-3-oxobutanamides on the behavior of the reaction was discovered. The key influence of ultrasonication and Lewis acid catalysts led to an established protocol to selectively obtain two or three types of heterocyclic scaffolds depending on the substituent in the N-aryl moiety.
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spelling pubmed-43116972015-02-10 The unexpected influence of aryl substituents in N-aryl-3-oxobutanamides on the behavior of their multicomponent reactions with 5-amino-3-methylisoxazole and salicylaldehyde Tkachenko, Volodymyr V Muravyova, Elena A Desenko, Sergey M Shishkin, Oleg V Shishkina, Svetlana V Sysoiev, Dmytro O Müller, Thomas J J Chebanov, Valentin A Beilstein J Org Chem Full Research Paper The switchable three-component reactions of 5-amino-3-methylisoxazole, salicylaldehyde and N-aryl-3-oxobutanamides under different conditions were studied and discussed. The unexpected influence of the aryl substituent in N-aryl-3-oxobutanamides on the behavior of the reaction was discovered. The key influence of ultrasonication and Lewis acid catalysts led to an established protocol to selectively obtain two or three types of heterocyclic scaffolds depending on the substituent in the N-aryl moiety. Beilstein-Institut 2014-12-17 /pmc/articles/PMC4311697/ /pubmed/25670972 http://dx.doi.org/10.3762/bjoc.10.320 Text en Copyright © 2014, Tkachenko et al. https://creativecommons.org/licenses/by/2.0https://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/2.0), 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
Tkachenko, Volodymyr V
Muravyova, Elena A
Desenko, Sergey M
Shishkin, Oleg V
Shishkina, Svetlana V
Sysoiev, Dmytro O
Müller, Thomas J J
Chebanov, Valentin A
The unexpected influence of aryl substituents in N-aryl-3-oxobutanamides on the behavior of their multicomponent reactions with 5-amino-3-methylisoxazole and salicylaldehyde
title The unexpected influence of aryl substituents in N-aryl-3-oxobutanamides on the behavior of their multicomponent reactions with 5-amino-3-methylisoxazole and salicylaldehyde
title_full The unexpected influence of aryl substituents in N-aryl-3-oxobutanamides on the behavior of their multicomponent reactions with 5-amino-3-methylisoxazole and salicylaldehyde
title_fullStr The unexpected influence of aryl substituents in N-aryl-3-oxobutanamides on the behavior of their multicomponent reactions with 5-amino-3-methylisoxazole and salicylaldehyde
title_full_unstemmed The unexpected influence of aryl substituents in N-aryl-3-oxobutanamides on the behavior of their multicomponent reactions with 5-amino-3-methylisoxazole and salicylaldehyde
title_short The unexpected influence of aryl substituents in N-aryl-3-oxobutanamides on the behavior of their multicomponent reactions with 5-amino-3-methylisoxazole and salicylaldehyde
title_sort unexpected influence of aryl substituents in n-aryl-3-oxobutanamides on the behavior of their multicomponent reactions with 5-amino-3-methylisoxazole and salicylaldehyde
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4311697/
https://www.ncbi.nlm.nih.gov/pubmed/25670972
http://dx.doi.org/10.3762/bjoc.10.320
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