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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Detalles Bibliográficos
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
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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
Descripción
Sumario: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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