Expedient Synthesis of Biginelli-Type Dihydropyrimidinones Using α-(Benzotriazolyl)alkyl Urea Derivatives

Abdel‐Fattah, Ashraf A. A.

doi:10.1055/s-2003-42398

Cited by 19 publications

(7 citation statements)

References 24 publications

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“…In order to exploit its synthetic potential, the original cyclocondensation has been extended widely to include variations in all three components. Meldrum’s acid and barbituric acid derivatives,117 or benzocyclic ketones and substituted α‐keto acids118 have been used as alternative substrates, for example, while substituted ureas proved able to replace the urea component,119 affording some novel drug‐like dihydropyrimidinone scaffolds in good to excellent yields. The aldehyde component has been widely varied, including not only many aromatic, but also aliphatic and heterocyclic aldehydes.…”

Section: Biginelli Dihydropyrimidine Synthesesmentioning

confidence: 99%

Utilisation of 1,3‐Dicarbonyl Derivatives in Multicomponent Reactions

2004

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Although isocyanide‐based multicomponent reactions (MCRs), introduced in 1921 by Passerini, largely predominate nowadays in the construction of widely diverse heterocycles, one of the first substrate classes involved in a MCR was that of 1,3‐dicarbonyl derivatives, with Hantzsch’s dihydropyridine synthesis appearing as early as 1882. The aim of this microreview is to present an overview of the great synthetic potential of MCRs involving the specific reactivity of easily accessible 1,3‐dicarbonyl derivatives and to stress their more recent utilisation for the development of new and useful methodologies valuable for the selective construction of highly functionalised small organic molecules of high synthetic and biological value. After a short general introduction, we present chronologically the different methodologies developed on the bases of the reactivity of 1,3‐dicarbonyl systems towards many other substrates involved in a variety of synthetic pathways, including Knoevenagel condensations, Michael and Mannich reactions, cyclodehydrations, electrocyclisations, cycloadditions and metal‐promoted transformations. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

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Section: Biginelli Dihydropyrimidine Synthesesmentioning

confidence: 99%

Utilisation of 1,3‐Dicarbonyl Derivatives in Multicomponent Reactions

2004

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“…Filtration followed by washing with cold MeOH and drying under vacuum afforded the product 1c as a yellow powder (1.00 g, 85 %); m.p. 118–120 °C (Lit . 117–119 °C).…”

Section: Methodsmentioning

confidence: 99%

Enantioselective N‐Acylation of Biginelli Dihydropyrimidines by Oxidative NHC Catalysis

et al. 2020

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“…Since dihydropyrimidinones display good biological activity, synthesis of their derivatives has been the very interesting field for the researchers working in the area of organic, medicinal chemistry, and related fields. [2][3][4] A number of multistep reactions have been developed and reported by researchers starting with aldehydes [5] or acetoacetate [6] equivalents in Biginelli-type reactions.…”

Section: Introductionmentioning

confidence: 99%

Biginelli‐type reaction: Efficient synthesis of 5‐unsubstituted 3,4‐dihydropyrimidin‐2‐ones and thiones fromgem‐dibromomethylarenes

Vinaya¹,

Kotturappa²,

Manjunath³

et al. 2020

Journal of Heterocyclic Chem

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In the present study, we are reporting a simple and efficient method for the one‐pot synthesis of the biologically important heterocyclic molecules 5‐unsubstituted 3,4‐dihydropyrimidin‐2‐ones and thiones using gem‐dibromomethylarenes, oxalacetic acid, and urea or thiourea. Gem‐dibromomethylarenes are used as aldehyde equivalent for the efficient synthesis of 3,4‐dihydropyrimidin‐2‐ones/thiones. This reaction offers advantages for the synthesis of these compounds, including ready availability of the starting materials, experimental simplicity and in good yields. Besides, the synthesized molecules are interesting for their biological and pharmacological actions.

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Expedient Synthesis of Biginelli-Type Dihydropyrimidinones Using α-(Benzotriazolyl)alkyl Urea Derivatives

Abstract: Reaction of readily available a-(benzotriazolyl)alkyl urea derivatives (derived from aromatic, heteroaromatic, and aliphatic aldehydes) with b-keto esters resulted in 3,4-dihydropyrimidin-2(1H)-ones in good to excellent yields.

Cited by 19 publications

References 24 publications

Utilisation of 1,3‐Dicarbonyl Derivatives in Multicomponent Reactions

Utilisation of 1,3‐Dicarbonyl Derivatives in Multicomponent Reactions

Enantioselective N‐Acylation of Biginelli Dihydropyrimidines by Oxidative NHC Catalysis

Biginelli‐type reaction: Efficient synthesis of 5‐unsubstituted 3,4‐dihydropyrimidin‐2‐ones and thiones fromgem‐dibromomethylarenes

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