Synthesis of dihydropyrimidinones via Biginelli multi-component reaction

Narahari, Srinivasa Reddy; Reguri, Buchi Reddy; Omprakash, G.; Mukkanti, K.

doi:10.1016/j.tetlet.2011.12.134

Cited by 67 publications

(24 citation statements)

References 41 publications

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“…In recent years, a number of methods have been developed to effectively accomplish the synthesis of these compounds, such as using various Brønsted acids , Lewis acids , basic catalysts , polymer‐supported reagents , and nan catalysts . However, many of these reported protocols suffer from various drawbacks such as the use of expensive and highly corrosive catalysts, tedious separation procedures, and prolonged reaction times.…”

Section: Introductionmentioning

confidence: 99%

Efficient Catalytic Synthesis of 3,4‐Dihydropyrimidin‐2‐ones/thiones via Little Acidic Ionic Liquid Combined with Rapid Heating Ways

Guo-ping

Tian

Shi

2018

Journal of Heterocyclic Chem

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in Wiley Online Library (wileyonlinelibrary.com).Catalytic synthesis of 3,4-dihydropyrimidin-2(1H)-ones/thiones was efficiently promoted by as little as 2.5 mol% of Brønsted acidic ionic liquid [(CH 2 ) 3 SO 3 HMIM]HSO 4 catalyst loading via rapid heating ways. Interestingly, rapid heating effectively improved yields to avoid side products. Furthermore, the mechanism has been speculated that the reaction proceeds may be via rapidly one-step condensation rather than slowly step-by-step condensation. In addition, the catalyst can be recovered for repeated use (up to seven times), and a whole green reaction process adds to its practical applicability.

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Section: Introductionmentioning

confidence: 99%

Efficient Catalytic Synthesis of 3,4‐Dihydropyrimidin‐2‐ones/thiones via Little Acidic Ionic Liquid Combined with Rapid Heating Ways

Guo-ping

Tian

Shi

2018

Journal of Heterocyclic Chem

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“…Despite all of the improved methods, organic synthesis methods still have many drawbacks, such as the use of organic solvents, long reaction times, high costs, low yields, nonsustainable catalysts, and purification issues [34][35][36][37][38][39][40].…”

Section: Introductionmentioning

confidence: 99%

Green High-Yielding One-Pot Approach to Biginelli Reaction under Catalyst-Free and Solvent-Free Ball Milling Conditions

2016

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A simple, green, and efficient approach was used to synthesize 3,4-dihydropyrimidines derivatives. We showed that the application of the planetary ball milling method with a ball-to-reagent weight ratio of 8 for the Biginelli reaction provides 3,4-dihydropyrimidines derivatives with excellent yields (>98%) in a short reaction time from the one-pot, three-component condensation of aldehydes, ethyl acetoacetate, and urea (or thiourea).

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“…Ever since this reaction was discovered by the Italian chemist Pietro Biginelli [3], scientists have paid a great deal of attention to it due to the unique biological activities of Biginelli compounds. These are antihypertensive, antiviral, antitumor, antibacterial and antiflammatory agents [4], which are also the basic skeleton of some pharmaceuticals that are used to prevent or treat cancer and AIDS [5]. The first used catalyst in this reaction was HCl [3].…”

Section: Introductionmentioning

confidence: 99%

Investigating the effect of immobilization of yttrium-Schiff base onto magnetite nanoparticles: enhanced catalytic activity in the synthesis of dihydropyrimidinones under solvent-free conditions

Khomami

Heshmatpour

2015

Res Chem Intermed

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A new complex of yttrium-salpr was synthesized through the reaction of Y(NO 3 ) 3 Á6(H 2 O) and salpr Schiff base (salpr = N,N 0 -bis(3-salicylidenaminopropyl) amine). The prepared complex was characterized by Mid and Far-IR, 13 C-NMR, 1 H-NMR, UV-Vis, XRF, and CHN. The obtained data suggested a binuclear structure for this compound. To our surprise, the catalytic activity of this complex was even lower than its precursor, Y(NO 3 ) 3 Á6(H 2 O), in one-pot synthesis of dihydropyrimidinones under solvent-free conditions. As one of the reasons of this reduced activity should pertain to the binuclear structure of the complex that reduces the availability of yttrium in the reaction, the complex was immobilized on modified Fe 3 O 4 nanoparticles, which not only increases the surface to the volume ratio of the compound, but also hinders the formation of binuclear structure due to site (Schiff base) isolation. These prepared nanoparticles depicted noticeably high catalytic activity as well as good recyclability and very easy separation.

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Synthesis of dihydropyrimidinones via Biginelli multi-component reaction

Cited by 67 publications

References 41 publications

Efficient Catalytic Synthesis of 3,4‐Dihydropyrimidin‐2‐ones/thiones via Little Acidic Ionic Liquid Combined with Rapid Heating Ways

Efficient Catalytic Synthesis of 3,4‐Dihydropyrimidin‐2‐ones/thiones via Little Acidic Ionic Liquid Combined with Rapid Heating Ways

Green High-Yielding One-Pot Approach to Biginelli Reaction under Catalyst-Free and Solvent-Free Ball Milling Conditions

Investigating the effect of immobilization of yttrium-Schiff base onto magnetite nanoparticles: enhanced catalytic activity in the synthesis of dihydropyrimidinones under solvent-free conditions

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