One-pot synthesis of pyrano[2,3-d]pyrimidinone derivatives catalyzed by L-proline in aqueous media

Bararjanian, Morteza; Balalaie, Saeed; Movassag, Barahman; Amani, Ali Mohammad

doi:10.1007/bf03245854

Cited by 98 publications

(29 citation statements)

References 11 publications

(10 reference statements)

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“…Step 5 Utilizing the above results, the simplified scheme of the proposed reaction mechanism (Scheme 2, [29][30][31]) as a possible explanation is shown in Figure 6 [14,18,37].…”

Section: Effects Of Concentrationmentioning

confidence: 99%

“…Strategies for the synthesis of these compounds have varied from one-pot to multistep approaches [13]. In recent years, the syntheses of pyrano [2,3-d]pyrimidine were reported using a plethora of reagents in the presence of catalyst, such as L-proline [14], microwave irradiation [15] [17], and diammonium hydrogen phosphate [18]. However, some of these methods have drawbacks, such as long reaction times, unsatisfactory yields.…”

Section: Introductionmentioning

confidence: 99%

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Kinetic and Mechanistic Investigation of Pyrano[2,3-d]pyrimidine Formation in the Presence of Catalyst under Novel One-Pot Three-Component Reaction

Habibi‐Khorassani

Maghsoodlou

Shahraki

et al. 2014

Organic Chemistry International

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Sodium acetate was applied as an efficient catalyst for the one-pot, three-component condensation reactions consisting of 4-nitrobenzaldehyde 2, malononitrile 3, and thiobarbituric acid 1. Use of nontoxic reaction components, short reaction times, environmental, easy work-up, and high yields are some remarkable advantages of this method. Kinetics and mechanism of the reaction were spectrally studied and the second order rate constant (k ovr = k 1 ) was automatically calculated by the standard equations contained within the program. The second order rate constant [Ln(k ovr = k 1 ), Ln(k ovr = k 1 )/T] that depended on reciprocal temperature was in good agreement with the Arrhenius and Eyring equations, respectively. This data provided the suitable plots for calculating the activation energy and parameters (Ea, ΔG ‡ , ΔS ‡ , and ΔH ‡ ) of the reaction. Furthermore, from studying the effects of solvent, concentration, and catalyst on the reaction rate, useful information was obtained regarding the mechanism. The results showed that the first step of the reaction mechanism is a rate determining step (RDS). The proposed mechanism was confirmed in accordance with the experimental data and also the steady state approximation.

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“…Step 5 Utilizing the above results, the simplified scheme of the proposed reaction mechanism (Scheme 2, [29][30][31]) as a possible explanation is shown in Figure 6 [14,18,37].…”

Section: Effects Of Concentrationmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Kinetic and Mechanistic Investigation of Pyrano[2,3-d]pyrimidine Formation in the Presence of Catalyst under Novel One-Pot Three-Component Reaction

Habibi‐Khorassani

Maghsoodlou

Shahraki

et al. 2014

Organic Chemistry International

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“…Therefore, for the preparation of these complex molecules large efforts have been directed towards the synthetic manipulation of uracils. As a result, a number of methods for the synthesis of these compounds have been reported (Rao et al, 1974;Junek et al, 1973;Noboru et al, 1973;Bararjanian et al, 2009;Ziarani et al, 2013), but the majority of them involve various steps, waste of organic solvents, long reaction time and the yields are relatively poor. This initiated to develop an efficient method for the synthesis of these compounds in better yields.…”

Section: Introductionmentioning

confidence: 99%

One step cyclocondensation of (thio) barbituric acid with chalcones in glacial acetic acid and phosphorous pentoxide, Part-II

Akhter

Halim

Ahmed

et al. 2017

Bangladesh J. Sci. Ind. Res.

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A number of new 5, 7-diaryl-1,5-dihydro (or 1, 2, 3, 5-tetrahydro)-pyrano [2, 3-d] pyrimidin-2, 4-diones (or 2-thioxo-4-ones) (3a-g) have been synthesized in one-step by cyclocondensation of barbituric acid or thiobarbituric acid (1) with arylideneacetophenones (2a-d), in glacial acetic acid in the presence of phosphorous pentoxide. The structures of the compounds 3a-g have been determined by UV, IR, 1H NMR, 13C NMR, mass spectral data and elemental analyses. The compounds 3a-g do not seem to be available in the literature.

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“…In1893, Pietro Biginelli reported synthesis of 4-dihydropyrimidin-2(1H)-one by cyclocondensation of ethyl acetoacetate, benzaldehyde, and urea by simply heating a mixture of these three components in the presence of acid as a catalysts under reflux conditions [10]. [18] , amino acid catalyzed [19], [20], 21], Mesoporous SBA-15 nanoparticles [22] and Quaternary Ammonium-treated clay in water catalyzed [23]synthesis of DHPMs. Drawbacks of these classical methods and catalytic efficacy of environmental benign catalyst gave us a direction to introduce new efficient catalysts for prepration of 4-aryl-3,4-dihydropyrimidin-2(1H)-ones with cost effectiveness and mild conditions with high yields.…”

Section: Introductionmentioning

confidence: 99%

Environmentally Benign Syntheses and Characterization of 4- Aryldihydropyrimidin-2(1H)-ones

Shafqat

Khan

et al. 2016

MATEC Web Conf.

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Abstract.A general, simple, efficient, cost-effective and environmental benign procedure for the syntheses of 4-aryl-3,4-dihydropyrimidin-2(1H)-ones (DHPMs) has been developed. The reaction is efficiently catalysed by using various amino acids viz., glycine, L-proline, L-cysteine, leucine and tryptophan. Reactions give excellent yields under reflux conditions. The chemical structures of these compounds were identified by Fourier Transform-Infra Red Spectroscopy (FT-IR), Gas Chromatography-Mass Spectroscopy (GC-MS) and Nuclear Magnetic Resonance Spectroscopy ( 1 H NMR). Physical parameters such as m.p., mixed m.p. as well as TLC also helped to characterize the expected products. The progress of the reaction time and purity was checked by TLC and the products were purified by recrystallization using ethyl acetate as a solvent. The synthesized molecule has numerous biological applications as it is anti-microbial, anti-inflammatory and anti-hypertensive in character.

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One-pot synthesis of pyrano[2,3-d]pyrimidinone derivatives catalyzed by L-proline in aqueous media

Abstract: An efficient protocol has been developed for the synthesis of various pyrano[2,3-d]pyrimidinones from condensation of aromatic aldehydes, malononitrile and barbituric-or thiobarbituric acid in aqueous ethanol using L-proline as a neutral bifunctional catalyst.

Cited by 98 publications

References 11 publications

Kinetic and Mechanistic Investigation of Pyrano[2,3-d]pyrimidine Formation in the Presence of Catalyst under Novel One-Pot Three-Component Reaction

Kinetic and Mechanistic Investigation of Pyrano[2,3-d]pyrimidine Formation in the Presence of Catalyst under Novel One-Pot Three-Component Reaction

One step cyclocondensation of (thio) barbituric acid with chalcones in glacial acetic acid and phosphorous pentoxide, Part-II

Environmentally Benign Syntheses and Characterization of 4- Aryldihydropyrimidin-2(1H)-ones

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