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.

Autor: Tkachenko VV; Division of Chemistry of Functional Materials, SSI 'Institute for Single Crystals' NAS of Ukraine, Lenin Ave. 60, Kharkiv 61001, Ukraine ; Faculty of Chemistry, V. N. Karazin Kharkiv National University, Svobody sq. 4, Kharkiv 61022, Ukraine., Muravyova EA; Division of Chemistry of Functional Materials, SSI 'Institute for Single Crystals' NAS of Ukraine, Lenin Ave. 60, Kharkiv 61001, Ukraine., Desenko SM; Division of Chemistry of Functional Materials, SSI 'Institute for Single Crystals' NAS of Ukraine, Lenin Ave. 60, Kharkiv 61001, Ukraine ; Faculty of Chemistry, V. N. Karazin Kharkiv National University, Svobody sq. 4, Kharkiv 61022, Ukraine., Shishkin OV; Division of Chemistry of Functional Materials, SSI 'Institute for Single Crystals' NAS of Ukraine, Lenin Ave. 60, Kharkiv 61001, Ukraine ; Faculty of Chemistry, V. N. Karazin Kharkiv National University, Svobody sq. 4, Kharkiv 61022, Ukraine., Shishkina SV; Division of Chemistry of Functional Materials, SSI 'Institute for Single Crystals' NAS of Ukraine, Lenin Ave. 60, Kharkiv 61001, Ukraine., Sysoiev DO; Fachbereich Chemie, University of Konstanz, Fach M-720, Universitaetsstrasse 10, D-78457 Konstanz, Germany., Müller TJ; Institut für Organische Chemie und Makromolekulare Chemie, Heinrich-Heine-Universität Düsseldorf, Universitätsstraße 1, D-40225 Düsseldorf, Germany., Chebanov VA; Division of Chemistry of Functional Materials, SSI 'Institute for Single Crystals' NAS of Ukraine, Lenin Ave. 60, Kharkiv 61001, Ukraine ; Faculty of Chemistry, V. N. Karazin Kharkiv National University, Svobody sq. 4, Kharkiv 61022, Ukraine ; Institut für Organische Chemie und Makromolekulare Chemie, Heinrich-Heine-Universität Düsseldorf, Universitätsstraße 1, D-40225 Düsseldorf, Germany.
Jazyk: angličtina
Zdroj: Beilstein journal of organic chemistry [Beilstein J Org Chem] 2014 Dec 17; Vol. 10, pp. 3019-30. Date of Electronic Publication: 2014 Dec 17 (Print Publication: 2014).
DOI: 10.3762/bjoc.10.320
Abstrakt: 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.
Databáze: MEDLINE
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