Effective Synthesis of 7‐Amino‐6‐cyano‐5‐aryl‐5H‐pyrano[2,3‐d]pyrimidine‐2,4(1H,3H)‐diones Under Microwave Irradiation

Gao, Yuan; Tu, Shujang; Li, Tuanjie; Zhang, Xiaojing; Zhu, Shaolin; Fang, Fang; Shi, Daqing

doi:10.1081/scc-120030318

Cited by 63 publications

(22 citation statements)

References 4 publications

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“…All products were known compounds and identified by comparing their spectra and all the physical data available in the literature [16,[29][30][31][32]36]. Melting points were measured by using the capillary tube method with an electro thermal 9200 apparatus.…”

Section: Methodsmentioning

confidence: 99%

H14[NaP5W30O110] catalyzed one-pot three-component synthesis of dihydropyrano[2,3-c]pyrazole and pyrano[2,3-d]pyrimidine derivatives

Heravi

Ghods

Derikvand

et al. 2010

JICS

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This is a report of an efficient, clean and facile method for the synthesis of 1,4-dihydropyrano[2,3-c] pyrazole and pyrano[2,3-d]pyrimidine derivatives via three-component one-pot condensation of 3-methyl-1-phenyl-1H-pyrazol-5(4H)-one or barbituric acid, aldehydes and malononitrile in the presence of a catalytic amount of preyssler type heteropolyacid as a green and reusable catalyst in water or ethanol under refluxing conditions.

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Section: Methodsmentioning

confidence: 99%

H14[NaP5W30O110] catalyzed one-pot three-component synthesis of dihydropyrano[2,3-c]pyrazole and pyrano[2,3-d]pyrimidine derivatives

Heravi

Ghods

Derikvand

et al. 2010

JICS

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“…Pyrano [2,3-d] [17], N-methylmorpholine [18], DAHP [19] [25]. Catalyst free procedure was also examined for the preparation of Pyrano [2,3-d]pyrimidine derivativies [26]. In addition, ultrasonic irradiation [27] and ballmilling technique [28] were used for the synthesis of Pyrano[2,3-d]pyrimidine derivativies.…”

Section: Introductionmentioning

confidence: 99%

Dibutylamine (DBA): A highly efficient catalyst for the synthesis of pyrano[2,3-d]pyrimidine derivatives in aqueous media

Bhat

Shalla

Dongre

2016

Journal of Taibah University for Science

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Annulated pyrano [2,3-d]pyrimidine derivatives were synthesized via one-pot three component condensation reactions of various aromatic aldehydes, malononitrile and barbituric acid in aqueous ethanol using dibutylamine (DBA) as catalyst. The potential application of DBA in organic synthesis increasing rapidly due to its reaction simplicity, minimum reaction time, high yields of the desired products (83-94%) and low cost chemicals. All the synthesized pyrano[2,3-d] pyrimidine derivatives were characterized by IR, 1 H NMR, 13 C NMR and mass spectra.

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“…Pyrano[2,3- d ]pyrimidine derivatives can be prepared by conjugate addition-cyclization of malononitrile to 5-arylidenebarbituric acids, or general procedures include the reaction of arylidenemalononitriles with barbituric acids under traditional hot reaction conditions [30, 31] or under microwave irradiation [32]. Recently, the synthesis of pyrano[2,3- d ]pyrimidines by simply ball-milling a stoichiometric mixture of an aldehyde, malononitrile, and barbituric acids without any catalyst or solvent was described [33].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of fused uracils: pyrano[2,3-d]pyrimidines and 1,4-bis(pyrano[2,3-d]pyrimidinyl)benzenes by domino Knoevenagel/Diels-Alder reactions

Pałasz

2012

Monatsh Chem

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Knoevenagel condensation of barbituric acids with aromatic aldehydes containing one or two formyl groups was carried out. 5-Arylidenebarbituric acids underwent smooth hetero-Diels-Alder (HDA) reactions with enol ethers to afford cis and trans diastereoisomers of pyrano[2,3-d]pyrimidine-2,4-diones and 5,5′-(1,4-phenylene)bis[2H-pyrano[2,3-d]pyrimidine-2,4(3H)-dione] derivatives in excellent yields (75–88 %). Syntheses were realized by Knoevenagel condensation and HDA reaction in four different reaction conditions: Knoevenagel condensation in water and Diels-Alder reaction in methylene chloride solution, Knoevenagel condensation in water and Diels-Alder reaction without solvent, three-component one-pot reaction in methylene chloride solution, or three-component one-pot reaction in water. All reactions were carried out without catalyst at room temperature. The reactions of malononitrile with Knoevenagel condensation products of barbituric acids and heteroaromatic aldehydes or terephthalaldehyde were examined and did not provide corresponding pyranopyrimidines.Graphical Abstract.

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Effective Synthesis of 7‐Amino‐6‐cyano‐5‐aryl‐5H‐pyrano[2,3‐d]pyrimidine‐2,4(1H,3H)‐diones Under Microwave Irradiation

Cited by 63 publications

References 4 publications

H14[NaP5W30O110] catalyzed one-pot three-component synthesis of dihydropyrano[2,3-c]pyrazole and pyrano[2,3-d]pyrimidine derivatives

H14[NaP5W30O110] catalyzed one-pot three-component synthesis of dihydropyrano[2,3-c]pyrazole and pyrano[2,3-d]pyrimidine derivatives

Dibutylamine (DBA): A highly efficient catalyst for the synthesis of pyrano[2,3-d]pyrimidine derivatives in aqueous media

Synthesis of fused uracils: pyrano[2,3-d]pyrimidines and 1,4-bis(pyrano[2,3-d]pyrimidinyl)benzenes by domino Knoevenagel/Diels-Alder reactions

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