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

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

Beilstein J. Org. Chem. 2014, 10, 3019–3030, doi:10.3762/bjoc.10.320

• , Universitätsstraße 1, D-40225 Düsseldorf, Germany 10.3762/bjoc.10.320 Abstract 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. Keywords: 5-amino-3-methylisoxazole

• of another heterocyclic class, namely thiadiazolylaminochromane. Here we disclose our recent findings of three-component heterocyclizations involving 5-amino-3-methylisoxazole, salicylaldehyde and N-aryl-3-oxobutanamides that were found to differ from similar reactions of cyclic CH acids [13