One-pot synthesis of 5-carboxanilide-dihydropyrimidinones using etidronic acid

Savant, Mahesh M.; Bhuva, Chirag V.; Singh, Jyoti; Yogesh, T. Naliapara

doi:10.24820/ark.5550190.p003.774

Cited by 15 publications

(6 citation statements)

References 12 publications

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“…Dihydropyrimidinones 29 (69%-97% yield) were achieved by Pansuriya and colleagues via the reaction of N -phenyl-3-oxobutanamides 28 with urea 8 and aldehydes 21 in the presence of etidronic acid (Scheme 5). 20 Etidronic acid was found suitable for all types of aldehydes and provided good to excellent yields of products compared to PPA and PPE.…”

Section: Multicomponent Synthesismentioning

confidence: 95%

Recent synthetic methodologies for pyrimidine and its derivatives

Ibraheem¹,

Saddique²,

Aslam³

et al. 2018

Turk J Chem

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Pyrimidine derivatives are well known due to their remarkable pharmacological potential in various fields of science, and they are also present in some natural substances like DNA and RNA. These scaffolds manifest diversified biological activities such as antimicrobial, antiinflammatory, anti-HIV, antitubercular, antitumor, antineoplastic, and antimalarial. A pyrimidine ring is constructed when chalcones, amidines, guanidine, nitriles, isocyanates, urea, thiourea, and aminopyrazoles undergo condensation, coupling, or cyclization reactions. In this context, the present review illustrates a variety of novel and efficient synthetic approaches towards the synthesis of pyrimidine and its derivatives that were reported recently.

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Section: Multicomponent Synthesismentioning

confidence: 95%

Recent synthetic methodologies for pyrimidine and its derivatives

Ibraheem¹,

Saddique²,

Aslam³

et al. 2018

Turk J Chem

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“…More recently, in a number of works [ 40–42 ] it was found that etidronic acid (HEDP) proved to be a convenient “green” catalyst in 3‐component reactions of the formation of dihydropyrimidones using carbonyl compounds with an active methylene group, urea and aldehydes as under traditional conditions, [ 40,41 ] and under microwave synthesis. [ 42 ] However, examples of the use of HEDP as a catalyst in the reactions of 1, 2‐dicarbonyl compounds with ureas are still not known.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of glycolurils and hydantoins by reaction of urea and 1, 2‐dicarbonyl compounds using etidronic acid as a “green catalyst”

Бакибаев

Uhov

Malkov

et al. 2020

Journal of Heterocyclic Chem

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Most of the known methods for the synthesis of heterocyclic compounds have disadvantages, such as a long reaction time and aggressive conditions. We have developed a new, rather simple and efficient method for the synthesis of a number of glycoluryls and hydantoins in water using a etidronic acid (HEDP) as "Green catalyst." So, for the first time, the condensation reaction of ureas with 1, 2-dicarbonyl compounds was carried out in the presence of HEDP. Also based on NMR studies, a chemism of these reactions, which is stepwise, is proposed. It has been established that the optimal conditions for the synthesis of glycoluryls and hydantoins using HEDP are: temperature 80 C-90 C, 40-20 minutes, and the ratio of urea and HEDP is 1:1. In all cases, the remaining aqueous filtrate containing HEDP after the reaction can be reused for other cycles synthesis of glycoluril and other compounds, because HEDP is not converted during the reaction.

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“…During the last decade, we have been involved in a program aimed at exploring the synthetic potential of 3-oxobutanamide derivative 1 as building blocks for polyfunctionally substituted hetero-aromatics. [1][2][3][4][5][6][7] Heterocyclic compounds possess a wide variety of important biochemical effects and pharmacological properties. Most of the heterocyclic Compounds are containing nitrogen, oxygen and sulfur possess broad spectrum of biological activity such as anti-bacterial and anti-fungal, [8,9] antiviral, [10] anti-inflammatory, [11] and anti-tumor drugs.…”

Section: Introductionmentioning

confidence: 99%

3‐Oxobutanamides in Heterocyclic Synthesis, Synthesis Approaches for new Pyridines, Pyrimidines and their Fused Derivatives

et al. 2017

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Condensation of 3‐oxobutanamide derivative 1 with DMF‐DMA afforded the thiazolopyrimidines 4, pyridine derivative 7 and naphthyridines 12 depending on the different reaction conditions. Condensation of 1 with triethylorthoformate afforded ethoxymethylene derivative 3. The ethoxymethylenes 3 reacted with different nucleophilic reagents to yield 14, 15, 20 and 23–25 respectively. Also, it reacted with malononitrile and ethyl cyanoacetate to give pyridine derivatives 28 a,b. Finally, the ethoxymethylenes 3 reacted with β‐naphthol to yield the benzoquinoline derivative 34.

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One-pot synthesis of 5-carboxanilide-dihydropyrimidinones using etidronic acid

Abstract: A combination of a modified Biginelli reaction and an etidronic acid prompted a cyclocondensation reaction providing 5-carboxanilide-dihydropyrimidinones in good to excellent yields.

Cited by 15 publications

References 12 publications

Recent synthetic methodologies for pyrimidine and its derivatives

Recent synthetic methodologies for pyrimidine and its derivatives

Synthesis of glycolurils and hydantoins by reaction of urea and 1, 2‐dicarbonyl compounds using etidronic acid as a “green catalyst”

3‐Oxobutanamides in Heterocyclic Synthesis, Synthesis Approaches for new Pyridines, Pyrimidines and their Fused Derivatives

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