Synthesis, optical properties, dyeing study of dihydropyrimidones (DHPMs) skeleton: Green and regioselectivity of novel Biginelli scaffold from Lawsone

Patil, Sharad R.; Choudhary, Amol S.; Patil, Vikas; Sekar, Nagaiyan

doi:10.1007/s12221-015-5233-x

Cited by 38 publications

(22 citation statements)

References 61 publications

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“…A number of recent studies explored the similarity and competition between the Hantzsch and Biginelli reactions, which can be exploited to obtain both classes of product libraries by using the same laboratory setup, thus representing a unique case in MCRs. Despite the vast literary output describing the mechanism of the Hantzsch and Biginelli reactions and the possible applications of 1,4-DHP and DHPM scaffolds, [12][13][14][15][16][17][18][19][20][21] a review focusing on their competition is nowhere to be found The aim of this review is to disclose the possibility of using the similarity and competition between the Hantzsch and Biginelli reactions in a practical way, which offers an organic solution. To this extent, a brief survey on both reaction mechanisms is provided.…”

Section: Introductionmentioning

confidence: 99%

Similarity and Competition between Biginelli and Hantzsch Reactions: an Opportunity for Modern Medicinal Chemistry

2020

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Similarity and competition between multicomponent reactions with similar mechanisms and leading to similar scaffolds can be a useful tool for medicinal chemistry. In this review, we have summarized the studies disclosing the mechanism of such competition between the Biginelli and Hantzsch reactions. We focused our attention in particular on those studies exploiting similarity and competition as an opportunity to switch from one reaction to another, by simply changing the reaction conditions, thus opening the possibility to obtain, using the same experimental setup, molecular libraries of both 3,4‐dihydropyrimidin‐2‐(1H)‐ones (DHPM) and 1,4‐dihydropyridines (1,4‐DHP) scaffolds. The aim of this review is to encourage further exploitation of such synthetic strategy as a tool for enhancing the chemical space in medicinal chemistry.

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Section: Introductionmentioning

confidence: 99%

Similarity and Competition between Biginelli and Hantzsch Reactions: an Opportunity for Modern Medicinal Chemistry

2020

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“…Indeed, they are versatile and crucial building blocks in organic synthesis and recognized as a new lead for drug discovery [15][16][17][18][19][20][21][22][23][24]. Despite their fascinating pharmaceutical applications, DHPMs have also been found in the development of functional materials, such as polymers, adhesives, optical materials, and dyes [32][33][34].…”

Section: Introductionmentioning

confidence: 99%

FeF3 as a green catalyst for the synthesis of dihydropyrimidines via Biginelli reaction

Krishna

Eppakayala²,

Kalita

2020

Eur J Chem

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A facile and highly efficient FeF3-catalyzed method has been developed for the direct synthesis of functionalized dihydropyrimidines from readily available starting materials via Biginelli reaction. These reactions proceed at low-catalyst loadings with high functional group tolerance under mild conditions. This method provides efficient reusability of the catalyst and good to excellent yields of the products, making the protocol more attractive, economical, and environmentally benign. FeF3 is an attractive catalyst for the Biginelli reaction because of its high acidity, thermal stability and water tolerance.

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“…Dihydropyrimidinone/thiones annulated heterocyclic scaffolds represent a privileged structural motif with a broad spectrum of significant biological activities 4,5 . A brief overview 6 features on the stimulated resurgence on the interest of dihydropyrimidones (DHPMs) ranging from their pharmacological activities such as antimalarial 7 , antitubercular 8 , A 2B adenosine receptor antagonists 9 , anticancer 10 , antihypertensive 11 , anti-inflammatory 12 , calcium channel modulators 13 , cardio vascular activity 14 , its wide presence in diverse natural products 15 and increasing applications in the development of materials such as renewable polymers 16 , adhesives 17 , fabric dyes 18 has been vastly explored. The reaction mechanism was discussed in various experimental and theoretical studies 19,20 .…”

Section: Introductionmentioning

confidence: 99%

“…The reaction mechanism was discussed in various experimental and theoretical studies 19,20 . Recent times have witnessed the exploitation of Biginelli reaction in asymmetric synthesis 21,22 , solid phase synthesis for combinatorial chemistry 23 , chemical biology 24 and optical properties 18 . Literature review reveals the versality of modifications on the combinatorial protocol of the reactants, catalyst, solvents, temperature and reaction conditions in order to increase the efficiency of the process.…”

Section: Introductionmentioning

confidence: 99%

Facile Ecofriendly One Pot Synthesis of Heterocyclic Priviledged Medicinal Scaffolds via Biginelli Reaction Using Retrievable Nickel Nanoparticles as Catalyst

Paul

Reddy

Rajendran

2018

J. Chil. Chem. Soc.

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An efficient and greener synthesis of a series of dihydropyrimidone (DHPMs)/ dihydropyrimithione (DHPMTs) derivatives were accomplished via three component one pot condensation between quinoline aldehyde (2-hydroxy-4-formyl quinoline/2-formyl-4-methoxy quinoline) , β -keto ester (ethyl acetoacetate / methyl acetoacetate) and urea/ thiourea using nickel(II) exchanged zeolite [Ni(II)Y] (NiNPs). The NiNPs were characterized by Infrared spectroscopy, Powder X ray diffraction patterns, Electronic microscopy studies-Scanning Electron Microscopy (FESEM) and Transmission Electron Microscopy (TEM). After the course of the reaction, the NiNPs were recovered and reused without any apparent loss of activity. The newly synthesized compounds were screened for antimicrobial activity against two human bacterial pathogens, the Gram-positive Methicillin resistant Staphylococcus aureus (MRSA) and the Gram-negative Pseudomonas aeruginosa (MTCC 201) and a human yeast pathogen, Fluconazole resistant Candida albicans (FRCA). The synthesised compounds were also evaluated for their antioxidant activity and the compounds show significant scavenging activity compared to aspartic acid.

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Synthesis, optical properties, dyeing study of dihydropyrimidones (DHPMs) skeleton: Green and regioselectivity of novel Biginelli scaffold from Lawsone

Cited by 38 publications

References 61 publications

Similarity and Competition between Biginelli and Hantzsch Reactions: an Opportunity for Modern Medicinal Chemistry

Similarity and Competition between Biginelli and Hantzsch Reactions: an Opportunity for Modern Medicinal Chemistry

FeF3 as a green catalyst for the synthesis of dihydropyrimidines via Biginelli reaction

Facile Ecofriendly One Pot Synthesis of Heterocyclic Priviledged Medicinal Scaffolds via Biginelli Reaction Using Retrievable Nickel Nanoparticles as Catalyst

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