An efficient multicomponent reaction for synthesis of 4-amino-6-aryl-2-alkylthiopyrimidine-5-carbonitrile derivatives

Rong, Liangce; Sheng, Xia; Yin, Shou-Wei; Tao, Shimin; Zha, Yunyun; Tu, Shu‐Jiang

doi:10.1007/s11164-012-0873-6

Cited by 5 publications

(3 citation statements)

References 15 publications

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“…The synthones 1,6-dihydro-2-methylthio-6oxo-4-arylpyrimidine-5-carbonitriles 4a-i were prepared by multicomponent reaction of araldehydes 1a-i, S-methylisothiourea sulfate 2 and ethyl cyanoacetate 3 by reflux in ethanol containing sodium hydroxide. (Rong et al, 2013) Heating of compounds 4a-i with ethanolamine 7 under solvent free condition at 130-140 °C for 3 hour afforded 1,6dihydro-2-(2-hydroxyethylamino)-6-oxo-4arylpyrimidine-5-carbonitriles 8a-i. This is a simple green with high yield and easily purified condition method.…”

Section: Results and Discussion: Chemistrymentioning

confidence: 99%

“…Compounds yields given are those of crude products. Ethyl cyanooacetate was purchased from s.d.fine limited Co., malononitrile was purchased from Acros Co., Compounds 5a-i (Rong et al, 2013;Hussein et al, 2011;Agarwal et al, 2002) and 6a-i (Kumar, 2008;Rong et al, 2012;Rostamizadeh and Nojavan, 2014) were prepared according to reported methods. (Rong et al, 2013;Rong et al, 2012) All solvents were obtained from commercial suppliers and used without further purification.…”

Section: Materials and Methods: Chemistrymentioning

confidence: 99%

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Design and synthesis of newly substituted 2-(2-Hydroxyethylamino)pyrimidine-5-carbonitrile with potential anticancer and antimicrobial activities

Abdel‐Aziz

2016

Zagazig Journal of Pharmaceutical Sciences

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A series of 1,6-dihydro-2-hydroxyethylamino-6-oxo-4-arylpyrimidine-5-carbonitriles 8a-i, and 4-amino-2-hydroxyethylamino-6-arylpyrimidine-5-carbonitriles 9a-i were prepared. Multicomponent reaction of araaldehyde 1a-i , S-methylisothiourea sulfate 2 with ethyl cyanoacetate 3 afforded 1,6-dihydro-2-methylthio-6-oxo-4-arylpyrimidine-5-carbonitriles 4a-i. Also, multicomponent reaction of 1, 2 with malononitrile 5 afforded 4-amino-2-methylthio-6arylpyrimidine-5-carbonitriles 6a-i. Reaction of compounds 4a-i, and 6a-i with ethanolamine 7 under solvent free condition at 130-140 °C afforded 8a-i, and 9a-i respectively. The purity of the new compounds was checked by TLC and elucidation of their structures was confirmed by IR, 1 H-NMR, 13 C-NMR and HRMS spectrometry. Compounds were subjected to NCI in vitro assessment for their anticancer activity at a single dose of 10 µM of test compounds, Also, all of the tested compounds were in vitro assessment for their antibacterial and antifungal activities in a comparison to chloramphenicol and clotrimazole as reference antibacterial and antifungal drugs respectively. All the tested compounds showed varied anticancer activities ranging from weak to moderate activities. In the other hand, most of them showed moderate antibacterial activities without any antifungal activities.

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Section: Results and Discussion: Chemistrymentioning

confidence: 99%

Section: Materials and Methods: Chemistrymentioning

confidence: 99%

Design and synthesis of newly substituted 2-(2-Hydroxyethylamino)pyrimidine-5-carbonitrile with potential anticancer and antimicrobial activities

Abdel‐Aziz

2016

Zagazig Journal of Pharmaceutical Sciences

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“…Until today, a number of methods have been reported for the synthesis of pyrimidine rings by the use of 1,3-binucleophilic centers such as guanidine, amidines, urea, and thiourea [30][31][32][33][34]. Recently, Rong [35] reported the synthesis of similar types of thiosubstituted pyrimidine derivatives, while Sheibani et al [36] synthesized some pyrimidine derivatives via multicomponent reaction using MgO as a catalyst. The reported methods have their own merits and demerits.…”

Section: Introductionmentioning

confidence: 99%

One-pot synthesis and in vivo biological evaluation of new pyrimidine privileged scaffolds as potent anti-inflammatory agents

et al. 2015

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A simple methodology has been developed for the synthesis of diverse members of multifunctionalized 4-hydroxy-2-methyl-6-(phenyl)pyrimidine-5-carbonitrile derivatives via multicomponent reaction of aromatic aldehydes, ethyl cyanoacetate, and acetamidine hydrochloride using a quantitative amount of NaOH in dry DMF at 80°C in a single procedural step. The carbon skeleton of synthesized compounds resembles the bacimethrin, an antibiotic active against several yeast and bacteria. The anti-inflammatory activities of all the synthesized compounds were assessed on Wistar rats using diclofenac sodium as a standard reference. The compound AC1, 2, 5, 9, and AC10 showed promising anti-inflammatory activity (80-83 %) in comparison with diclofenac sodium (85 %) in the carrageenan-induced rat paw edema assay, which is the key finding of this article. Graphical Abstract The synthesized 4-hydroxy-2-methyl-6-(phenyl)pyrimidine-5-carbonitrile derivatives shown promising anti-inflammatory activity (80-83 %) in comparison with diclofenac sodium (85 %) in the carrageenan-induced rat paw edema assay.Electronic supplementary material The online version of this article (

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An Efficient and Facile Synthesis of 5‐(Thiophene‐2‐carbonyl)‐6‐(trifluoromethyl)‐tetrahydro‐pyrimidin‐2(1H)‐one and 6‐(Thiophen‐2‐yl)‐4,5‐dihydropyrimidin‐2(1H)‐one from Same Substrates Under Different Conditions

Rong

Zha

Sheng

et al. 2014

Journal of Heterocyclic Chem

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A series of 5‐(thiophene‐2‐carbonyl)‐6‐(trifluoromethyl)‐tetrahydropyrimidin‐2(1H)‐one and 6‐(thiophen‐2‐yl)‐4,5‐dihydropyrimidin‐2(1H)‐one derivatives have been synthesized from the reactions of aromatic aldehydes, 4,4,4‐trifluoro‐1‐(thien‐2‐yl)butane‐1,3‐dione and urea under the different conditions with high yields. In this research, it was found that the p‐toluenesulfonic acid was an efficient catalyst for obtaining 5‐(thiophene‐2‐carbonyl)‐6‐(trifluoromethyl)‐tetrahydropyrimidin‐2(1H)‐one derivative. At the same time, solvent‐free and NaOH were the preferred conditions for the synthesis of 6‐(thiophen‐2‐yl)‐4,5‐dihydropyrimidin‐2(1H)‐one derivative. Moreover, because of short reaction time, excellent yields, simple setup, this research offered an efficient process for preparing these kind compounds.

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An efficient multicomponent reaction for synthesis of 4-amino-6-aryl-2-alkylthiopyrimidine-5-carbonitrile derivatives

Cited by 5 publications

References 15 publications

Design and synthesis of newly substituted 2-(2-Hydroxyethylamino)pyrimidine-5-carbonitrile with potential anticancer and antimicrobial activities

Design and synthesis of newly substituted 2-(2-Hydroxyethylamino)pyrimidine-5-carbonitrile with potential anticancer and antimicrobial activities

One-pot synthesis and in vivo biological evaluation of new pyrimidine privileged scaffolds as potent anti-inflammatory agents

An Efficient and Facile Synthesis of 5‐(Thiophene‐2‐carbonyl)‐6‐(trifluoromethyl)‐tetrahydro‐pyrimidin‐2(1H)‐one and 6‐(Thiophen‐2‐yl)‐4,5‐dihydropyrimidin‐2(1H)‐one from Same Substrates Under Different Conditions

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