Publikation:

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

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Datum

2014

Autor:innen

Tkachenko, Volodymyr V.
Muravyova, Elena A.
Desenko, Sergey M.
Shishkin, Oleg V.
Shishkina, Svetlana V.
Müller, Thomas J. J.
Chebanov, Valentin A.

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http://nbn-resolving.de/urn:nbn:de:bsz:352-0-269745
DOI (zitierfähiger Link)
https://doi.org/10.3762/bjoc.10.320
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Attribution 2.0 Generic

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Chemie: Publikationen
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Published

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Beilstein Journal of Organic Chemistry. 2014, 10, pp. 3019-3030. eISSN 1860-5397. Available under: doi: 10.3762/bjoc.10.320

Zusammenfassung

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.

Zusammenfassung in einer weiteren Sprache

Fachgebiet (DDC)
540 Chemie

Schlagwörter

5-amino-3-methylisoxazole, catalysis, chemoselectivity, heterocycle, multicomponent reaction, ultrasonication, salicylaldehyde

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ISO 690TKACHENKO, Volodymyr V., Elena A. MURAVYOVA, Sergey M. DESENKO, Oleg V. SHISHKIN, Svetlana V. SHISHKINA, Dmytro SYSOIEV, Thomas J. J. MÜLLER, Valentin A. CHEBANOV, 2014. 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. In: Beilstein Journal of Organic Chemistry. 2014, 10, pp. 3019-3030. eISSN 1860-5397. Available under: doi: 10.3762/bjoc.10.320
BibTex
@article{Tkachenko2014unexp-30506,
  year={2014},
  doi={10.3762/bjoc.10.320},
  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},
  volume={10},
  journal={Beilstein Journal of Organic Chemistry},
  pages={3019--3030},
  author={Tkachenko, Volodymyr V. and Muravyova, Elena A. and Desenko, Sergey M. and Shishkin, Oleg V. and Shishkina, Svetlana V. and Sysoiev, Dmytro and Müller, Thomas J. J. and Chebanov, Valentin A.}
}
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