Ferric chloride/tetraethyl orthosilicate as an efficient system for synthesis of dihydropyrimidinones by Biginelli reaction

Cepanec, Ivica; Litvić, Mladen; Bartolinčić, Anamarija; Lovrić, Marija

doi:10.1016/j.tet.2005.02.059

Cited by 72 publications

(22 citation statements)

References 39 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The dihydropyrimidinone core and its derivatives form an important class of compounds, as it is present in a large family of natural products with broad biological activities as antihypertensive, antiviral, antitumor and anti-inflammatory agents and as calcium channel blockers [15]. Attempts to synthesize these moieties by the Biginelli reaction over various heterogeneous catalysts such as KSF [16], silica sulfuric acid [17] and more recently, the Lewis acids cerium (III) and indium(III) chloride [18], CuCl 2 H 2 O/CuSO 4 ·5H 2 O [19] and ferric chloride/tetraethyl orthosilicate system are reported [20]. Recently, sulfated zirconia and sulfated zirconia modified with metals have been used in organic transformations to obtain 3,4-dihydropyrimidin-2(1H)-ones, bis-(indoyl)methane derivatives, 2,3-dihydro-1H-1,5-benzodiazepines, diaryl sulfoxides, coumarins, diphenylureas and protected carbonyl compounds and ZrO 2 /pillared clay has been reported to be an efficient catalyst for solventless synthesis of dihydropyrimidinones [21].…”

Section: Introductionmentioning

confidence: 99%

Sulfated Zirconia-Catalyzed Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones (DHPMs) Under Solventless Conditions: Competitive Multicomponent Biginelli vs. Hantzsch Reactions

Ángeles-Beltrán¹,

Lomas‐Romero²,

Lara-Corona³

et al. 2006

Molecules

View full text Add to dashboard Cite

Abstract:The catalytic ability of ZrO 2 /SO 4 2-to promote solventless three-component condensation reactions of a diversity of aromatic aldehydes, urea or thoiurea and ethyl acetoacetate was studied. Products resulting from Hantzsch and/or Biginelli multicomponent reactions are obtained in the presence of solid acid catalysts using the same reactants but different temperature conditions. The sulfated zirconia catalyst can be recovered and recycled in subsequent reactions with a gradual decrease of activity.

show abstract

Section: Introductionmentioning

confidence: 99%

Sulfated Zirconia-Catalyzed Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones (DHPMs) Under Solventless Conditions: Competitive Multicomponent Biginelli vs. Hantzsch Reactions

Ángeles-Beltrán¹,

Lomas‐Romero²,

Lara-Corona³

et al. 2006

Molecules

View full text Add to dashboard Cite

show abstract

“…However this reaction suffers from the harsh conditions, high raction times and frequently low yields Aryl substituted 3,4-dihydropyrimidine-2-(1H)-ones 3 and their derivatives are an important class of substances in organic and medicinal chemistry. Many synthetic methods [4][5][6][7][8] for preparing these compounds have been reported including classical methods, microwave irradiation and by using Lewis acids as well as protic acids. The discovery of a new an inexpensive catalyst for the preparation of 3,4-dihydropyrimidine-2-(1H)-ones under neutral and mild conditions with high yield of prime importance.…”

Section: Introductionmentioning

confidence: 99%

Comparative Study of Chemical Synthesis of Pyrimidine Derivatives by Using Grindstone Chemistry Technique and Conventional Method

Sonawane

2014

ILCPA

View full text Add to dashboard Cite

The majority of the drugs on the market today are entirely chemically synthesized in the laboratory. Several scientists had synthesized dihydropyrimidine (DHPMs) derivatives showing a wide spectrum of biological actions as antibacterials, antivirals as well as antitumor agents. This activity is principally due to presence of steriogenic carbon C4 in their structure. The current investigation is comparative study of chemically synthesis of two DHPMs derivatives by Biginelli Reaction using conventional method and grindstone chemistry technique. The synthesis of DHPMs derivative involves a multicomponent reaction (aldehyde derivative, urea /thiourea and 1,3-dicarbonyl compounds) in presence of HCl / NH 4 Cl as a catalyst. Two derivative viz. 3,4-dihydropyrimidin-2-(1H)-ones and 3,4-dihydropyrimidin-2-(1H)-thiones were synthesized and characterized using IR. The melting points were obtained are 208 °C and 210 °C respectively. "Grindstone Chemistry Technique" catalyzed by CuCl 2 ·2H 2 O and Conc. HCl. gave more yield, solvent free and ecofriendly. The obtained products have been identified by comparison with spectral data & their melting points. This study will help to develop easy protocol for the synthesis of many more DHPMs derivative with high yield.

show abstract

“…Many synthetic methods [4][5][6][7][8] for preparing these compounds have been reported including classical methods, microwave irradiation and by using Lewis acids as well as protic acids. The discovery of a new an inexpensive catalyst for the preparation of 3,4-dihydropyrimidine-2-(1H)-ones under neutral and mild conditions with high yield of prime importance.…”

Section: Introductionmentioning

confidence: 99%

Green Synthesis of Pyrimidine Derivative

Sonawane

2013

ILCPA

View full text Add to dashboard Cite

The majority of the drugs on the market today are entirely chemically synthesized in the laboratory. Several scientists had synthesized dihydropyrimidine (DHPMs) derivatives showing a wide spectrum of biological actions as antibacterials, antivirals as well as antitumor agents. This activity is principally due to presence of steriogenic carbon C4 in their structure. The current investigation is study and synthesis of dihydropyrimidinones efficiently and in high yields under mild, solvent free and eco-friendly conditions by using "Grindstone Chemistry Technique" catalyzed by CuCl 2 ·2H 2 O and Conc. HCl. The obtained products have been identified by comparison with spectral data & their melting points. The synthesis of DHPMs derivative involves a multicomponent reaction (aldehyde derivative, urea /thiourea and 1,3-dicarbonyl compounds) in presence of HCl / NH 4 Cl as a catalyst. 3,4-dihydropyrimidin-2-(1H)-ones was synthesized and characterized using IR. The melting points was obtained 203 °C.

show abstract

Ferric chloride/tetraethyl orthosilicate as an efficient system for synthesis of dihydropyrimidinones by Biginelli reaction

Cited by 72 publications

References 39 publications

Sulfated Zirconia-Catalyzed Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones (DHPMs) Under Solventless Conditions: Competitive Multicomponent Biginelli vs. Hantzsch Reactions

Sulfated Zirconia-Catalyzed Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones (DHPMs) Under Solventless Conditions: Competitive Multicomponent Biginelli vs. Hantzsch Reactions

Comparative Study of Chemical Synthesis of Pyrimidine Derivatives by Using Grindstone Chemistry Technique and Conventional Method

Green Synthesis of Pyrimidine Derivative

Contact Info

Product

Resources

About