ChemInform Abstract: Multicomponent Heterocyclization Reactions with Controlled Selectivity

Чебанов, Валентин А.; Desenko, S. M.

doi:10.1002/chin.201246241

Cited by 4 publications

(2 citation statements)

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“…On the other hand, the application of thermal heating caused changing the multicomponent process' behavior: refluxing the starting materials 1 , 2 , and 3 in methanol (Scheme , Table , Entry 1) or ethanol (Entry 2) yielded the mixture of substances 4 and 5 . Similar results were observed when the starting reagents were fused in few drops of DMF (Entry 3). Therefore, this multicomponent heterocyclization was studied in details in order to direct it towards selective obtaining compounds 5 .…”

Section: Resultssupporting

confidence: 80%

Diversity‐oriented Multicomponent Heterocyclizations Involving Derivatives of 3(5)‐Aminoisoxazole, Aldehydes and Meldrum's or N,N′‐Dimethylbarbituric Acid

Морозова

Muravyova

Shishkina

et al. 2016

Journal of Heterocyclic Chem

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Section: Resultssupporting

confidence: 80%

Diversity‐oriented Multicomponent Heterocyclizations Involving Derivatives of 3(5)‐Aminoisoxazole, Aldehydes and Meldrum's or N,N′‐Dimethylbarbituric Acid

Морозова

Muravyova

Shishkina

et al. 2016

Journal of Heterocyclic Chem

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“…It should be firstly noted that the formation of any of the compounds 4 – 6a through the intermediate 7 (pathway A) as for cyclic 1,3-diketones [13,25] was excluded because the latter does not react with amide 3a under any comparable conditions.…”

Section: Resultsmentioning

confidence: 99%

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

Тkachenko¹,

Muravyova²,

Десенко³

et al. 2014

Beilstein J. Org. Chem.

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SummaryThe 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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Synthesis of Diheteroatomic Five‐Membered Heterocyclic Compounds from α,β‐Unsaturated Aldehydes

Keiko

Вчисло

2016

Asian J Org Chem

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The recent increasei ni nterest in the chemistry of azoles has been owing to their paramount importance in several essential fields of research, such as pharmacology, medicine, biology, the organic synthesis of fine chemicals, agriculturalc hemistry, and the chemical industry.T his Focus Review summarizes and highlights recently developed methods for the synthesis of five-membered N,N-, N,O-, andN ,Sheterocycles based on the transformations of 2-alkenals. Over the last 15 years, these reactions, which often differ from reactions involving other a,b-unsaturatedc arbonyl compoundsi nt erms of methoda nd results, have gathered significant momentum. The multitude of catalytic and tech-nological novelties discussed in this Focus Review,s uch as asymmetricm etal-and organocatalysis,o ne-pot multicomponent reactions that proceed through domino, cascade, or tandem sequences, and microwave activation,p romote the formation of ad iverse range of target products, the structures of which becomec lear from the mechanistic schemes given in this Focus Review.T he mechanisms discussed reflect great advances in the chemo-, regio-, and stereoselectivity of the reactions of 2-alkenals, which allows new azoles and related compounds (imidazoles, pyrazoles, oxazoles, thiazoles, and their hydrogenatedd erivatives) to be synthesized.[a] Prof.The ORCID identification number(s) for the author(s) of this articlecan be found under http://dx.Scheme2.One-potsynthesis of imidazoles 8 and tentativemechanism of the reaction.T s= 4-toluenesulfonyl, TMS = tert-butyltrimethylsilyl, Bn = benzyl, Lg = leaving group.Scheme3.Enantioselective synthesiso f3-hydroxyalkyl and 3-aminoalkyli midazo[1,2-a]pyridines (9)through an asymmetricorganocatalytic [3+ +2] annulation strategy.Alk = alkyl.Scheme4.One-potsynthesis of imidazole-containingc ondensed heterocycles by the reaction of 2-alkoxypropenalswith N-binucleophiles.Scheme9.Aroute to 2-(1'-alkoxyvinyl)imidazolidines 27 through the condensation of alkoxy propenals.

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ChemInform Abstract: Multicomponent Heterocyclization Reactions with Controlled Selectivity

Abstract: Review: 72 refs.

Cited by 4 publications

References 1 publication

Diversity‐oriented Multicomponent Heterocyclizations Involving Derivatives of 3(5)‐Aminoisoxazole, Aldehydes and Meldrum's or N,N′‐Dimethylbarbituric Acid

Diversity‐oriented Multicomponent Heterocyclizations Involving Derivatives of 3(5)‐Aminoisoxazole, Aldehydes and Meldrum's or N,N′‐Dimethylbarbituric Acid

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

Synthesis of Diheteroatomic Five‐Membered Heterocyclic Compounds from α,β‐Unsaturated Aldehydes

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