An efficient three-component synthesis of 3,4-dihydropyrimidinones using MCM-41 anchored sulfonic acid （MCM-41-R-SO3H） as a mild, heterogeneous catalyst for Biginelli reaction in CH3CN under reflux condition is desc...An efficient three-component synthesis of 3,4-dihydropyrimidinones using MCM-41 anchored sulfonic acid （MCM-41-R-SO3H） as a mild, heterogeneous catalyst for Biginelli reaction in CH3CN under reflux condition is described.展开更多
4-Aryl/alkyl-3,4-dihydro-2(1H)-pyrimidone esters and 5-acetyl-4-aryl/or alkyl-6-methyl- 3, 4-dihydropyrimidin-2(l)-ones were synthesised efficientiy using montmorillonite clay- SmCl3 6H2O system promoted by microwave ...4-Aryl/alkyl-3,4-dihydro-2(1H)-pyrimidone esters and 5-acetyl-4-aryl/or alkyl-6-methyl- 3, 4-dihydropyrimidin-2(l)-ones were synthesised efficientiy using montmorillonite clay- SmCl3 6H2O system promoted by microwave irradiation in solvenfless condition.展开更多
A highly efficient catalyst indium (III) tribromide is used to synthesize 5-alkoxy-carbonyl-4-hydrocarbyl-3,4-dihydropyrimidin-2(1H)-ones by a three-component coupling of beta-keto ester, aldehydes and urea through im...A highly efficient catalyst indium (III) tribromide is used to synthesize 5-alkoxy-carbonyl-4-hydrocarbyl-3,4-dihydropyrimidin-2(1H)-ones by a three-component coupling of beta-keto ester, aldehydes and urea through improved Biginelli reaction.展开更多
A Nation-H catalyzed, single step and environmentally friendly process for synthesis of dihydropyrimidinones is described. This adopted protocol for Biginelli reaction has the advantages of reusability of the catalyst...A Nation-H catalyzed, single step and environmentally friendly process for synthesis of dihydropyrimidinones is described. This adopted protocol for Biginelli reaction has the advantages of reusability of the catalyst, high yields and ease of separation of pure products.展开更多
The condensation of benzaldehyde, urea, and ethyl acetoacetate according to the procedure described by Biginelli was investigated at the B3LYP/6-31G（d）, B3LYP/6-31 ＋G（d,p）, and B3LYP/6-311＋G（3df,2p）//B3LYP/6-3...The condensation of benzaldehyde, urea, and ethyl acetoacetate according to the procedure described by Biginelli was investigated at the B3LYP/6-31G（d）, B3LYP/6-31 ＋G（d,p）, and B3LYP/6-311＋G（3df,2p）//B3LYP/6-31＋G（d,p） levels to explore the reaction mechanism. According to the mechanism proposed by Kappe, structures of five intermediates were optimized and four transition states were found. The calculation results proved that the mechanism proposed by Kappe is right.展开更多
A new method for the synthesis of 1-methylimidazolium trifluoroacetate ([Hmi]Tfa), a protic ionic liquid (PIL), under ultrasonic irradiation has been developed. In addition, the product [Hmi]Tfa was successfully emplo...A new method for the synthesis of 1-methylimidazolium trifluoroacetate ([Hmi]Tfa), a protic ionic liquid (PIL), under ultrasonic irradiation has been developed. In addition, the product [Hmi]Tfa was successfully employed as solvent and catalyst in Biginelli reaction to prepare 3,4-dihydropyrimidinones (DHPMs) in high yield under mild reaction conditions.展开更多
[Hmim][Tfa] was used as catalyst for the Biginelli reaction under microwave heating. Low catalyst loading, reduced reaction time and operational simplicity are the main highlights of this protocol. The proposed protoc...[Hmim][Tfa] was used as catalyst for the Biginelli reaction under microwave heating. Low catalyst loading, reduced reaction time and operational simplicity are the main highlights of this protocol. The proposed protocol was found active in the synthesis of 30 different biologically active compounds.展开更多
A simple, green and highly efficient procedure for the Biginelli condensation reaction of aldehydes, β-ketoesters, urea or thiourea catalyzed by crushed garlic clove at ambient temperature is reported.
4-Aryl-3, 4-dihydropyrimidinones were synthesized using microwave-assisted,solvent-free protocol of the Biginelli reaction. The simple method provides the title compounds in78%―95% yields by the reaction of aromatic ...4-Aryl-3, 4-dihydropyrimidinones were synthesized using microwave-assisted,solvent-free protocol of the Biginelli reaction. The simple method provides the title compounds in78%―95% yields by the reaction of aromatic aldehydes with ethyl acetoac-etate and urea/thiourea inthe presence of a catalytic amount of cone. HCl. Lewis acids, such as ZnCl_2, SnCl_2, FeCl_3·6H_2O,and CuCl_2·2H_2O, were also found to be efficient catalysts for the synthesis ofdihydropyrimidinones.展开更多
An efficient synthesis of 3,4-dihydropyrimidinones from aldehyde, β-ketoester and urea in ethanol using cobalt chloride hexahydrate or lanthanum chloride heptahydrate as acatalyst was described. Compared to the class...An efficient synthesis of 3,4-dihydropyrimidinones from aldehyde, β-ketoester and urea in ethanol using cobalt chloride hexahydrate or lanthanum chloride heptahydrate as acatalyst was described. Compared to the classical Biginelli reaction, this new method consistentlyhas the advantage of good yields (56%―99%) as well as short reaction tune (4―5 h).展开更多
The effect of addition of poly（ethylene glycol）-400 （PEG-400） and carbon （0, 1, 2 and 3 wt%） as substrates were investigated systematically to get the desired phase of carbon-doped MoO3 material. The carbon sour...The effect of addition of poly（ethylene glycol）-400 （PEG-400） and carbon （0, 1, 2 and 3 wt%） as substrates were investigated systematically to get the desired phase of carbon-doped MoO3 material. The carbon source was prepared from the Acacia arabica plant wood. The resulting samples were calcined at 500 ℃. The effect of PEG-400 and carbon composite on the structure, particle size and morphology were investigated. The prepared samples were characterized by XRD, SEM-EDS and FT-IR techniques. The samples with PEG-400 and carbon ad- dition give better control of particle size and porosity. The prepared catalysts were tested for the synthesis of 3,4-dihydropyrimidones via the Biginelli-type condensation reaction. This new method consistently has the advan- tage of excellent yields （88%--93%） and short reaction times （1.5--3 h） than do classical Biginelli reaction conditions.展开更多
The immobilized nickel(II) on the organic-inorganic hybrid material was prepared and used as an effective catalyst for the Biginelli reaction.In the presence of the immobilized nickel catalyst,aromatic aldehydes react...The immobilized nickel(II) on the organic-inorganic hybrid material was prepared and used as an effective catalyst for the Biginelli reaction.In the presence of the immobilized nickel catalyst,aromatic aldehydes reacted with ethyl acetoacetate and urea (or thiourea) smoothly to generate the corresponding Biginelli products in good to excellent yields without using any additive.The work-up procedure is very simple and practical.Furthermore,the silica-supported nickel(II) could be recovered and recycled for six consecutive trials without significant loss of its catalytic activity.展开更多
A series of novel supramolecular organocatalysts of hydroxyprolinamide based on the upper rim of calix[4]arene scaffold have been developed to catalyze enantioselective multi-component Biginelli reaction. Under the op...A series of novel supramolecular organocatalysts of hydroxyprolinamide based on the upper rim of calix[4]arene scaffold have been developed to catalyze enantioselective multi-component Biginelli reaction. Under the optimal conditions, the reactions occurred with moderate-to-excellent enantioselectivities (up to 98% ee). A plausible transition state constructed by the supra- molecular interaction of hydrogen bond and cation-π between catalysts and substrates has been proposed.展开更多
A facile and efficient protocol for the synthesis of 3,4-dihydropyrimidones via one-pot Biginelli reaction in PEG1000-DAIL/toluene system was developed. PEG1000-DAIL/toluene mixture is a temperature-driven reversible ...A facile and efficient protocol for the synthesis of 3,4-dihydropyrimidones via one-pot Biginelli reaction in PEG1000-DAIL/toluene system was developed. PEG1000-DAIL/toluene mixture is a temperature-driven reversible b/phasic system, which promises the fully display of catalytic activity and simple recycle of PEGI0oo-DAIL. As a re- suit, PEG1000-DAIL/toluene mixture showed catalyst-medium double-duty in the Biginelli reaction and afforded cor- responding 3,4-dihydropyrimidones in excellent yields of activity was observed even after 10 recycling, runs. 80%---95% for 20 examples. No obvious loss of catalytic展开更多
The low-cost CuBr-promoted domino Biginelli reaction among readily available ketones,salicylaldehyde derivatives and 3-amino-1,2,4-triazole was studied under solvothermal conditions,giving the novel bridged polyhetero...The low-cost CuBr-promoted domino Biginelli reaction among readily available ketones,salicylaldehyde derivatives and 3-amino-1,2,4-triazole was studied under solvothermal conditions,giving the novel bridged polyheterocycles bearing two or three stereocenters depending on the starting ketones.This multicomponent reaction proceeded with high diastereoselectivity(dr>20:1)based on a combined~1 H NMR,crystallographic and supercritical fluid chromatographic(SFC)analysis of the product.Time-dependent high-resolution mass spectrometry(HRMS)was performed to track the reaction process,and several key intermediates were identified,leading to the drawing of a plausible reaction mechanism.Density functional theory(DFT)calculation was supplemented,and two reaction pathways were differentiated.Moreover,in vitro antitumor activity was evaluated using HeLa and HepG2 cell lines,and two of these polyheterocycles demonstrated promising activities against HepG2 cells with EC50 down to 10μmol/L.Additionally,ESI-MS/MS studies on all the polyheterocycles suggest a common fragmentation pathway(loss of one molecule of amino-triazole)they shared,providing the first-hand fragmentation rules for future rapid structural identification of them.The multicomponent domino reaction presented here may offer prospects for future design of more efficient strategies to access medicinally important bridged polyheterocycles.展开更多
Recently, the Biginelli reaction, one of the most famous multicomponent reactions, has been introduced into the polymer chemistry to highly efficiently synthesize some interesting functional polymers. In this mini-rev...Recently, the Biginelli reaction, one of the most famous multicomponent reactions, has been introduced into the polymer chemistry to highly efficiently synthesize some interesting functional polymers. In this mini-review, several applications of the Biginelli reaction in polymer chemistry have been summarized, including polycondensation, post-polymerization modification,one-pot synthesis of well-defined polymer, etc. Meanwhile, the utilization of the Biginelli reaction in material science and chemical biology, and the future development of the Biginelli reaction in polymer chemistry have also been discussed.展开更多
A mild, simple and efficient procedure for the preparation of 3,4-dihydropyrimidin-2（1H）-ones and -thiones is described using N-sulfonic acid poly（4-vinylpyridinium） chloride （NSPVPC） as a heterogeneous and effi...A mild, simple and efficient procedure for the preparation of 3,4-dihydropyrimidin-2（1H）-ones and -thiones is described using N-sulfonic acid poly（4-vinylpyridinium） chloride （NSPVPC） as a heterogeneous and efficient catalyst under solvent-free conditions. Simple methodologies, easy work-up procedure, easy preparation of the catalyst, excellent yields and very short reaction times are among the other advantages of this work. Further, the catalyst can be reused and recovered for several times without significant decrease in its activity.展开更多
文摘An efficient three-component synthesis of 3,4-dihydropyrimidinones using MCM-41 anchored sulfonic acid （MCM-41-R-SO3H） as a mild, heterogeneous catalyst for Biginelli reaction in CH3CN under reflux condition is described.
文摘4-Aryl/alkyl-3,4-dihydro-2(1H)-pyrimidone esters and 5-acetyl-4-aryl/or alkyl-6-methyl- 3, 4-dihydropyrimidin-2(l)-ones were synthesised efficientiy using montmorillonite clay- SmCl3 6H2O system promoted by microwave irradiation in solvenfless condition.
基金the National Natural Science Foundation of China(29872018&29972026).
文摘A highly efficient catalyst indium (III) tribromide is used to synthesize 5-alkoxy-carbonyl-4-hydrocarbyl-3,4-dihydropyrimidin-2(1H)-ones by a three-component coupling of beta-keto ester, aldehydes and urea through improved Biginelli reaction.
文摘A Nation-H catalyzed, single step and environmentally friendly process for synthesis of dihydropyrimidinones is described. This adopted protocol for Biginelli reaction has the advantages of reusability of the catalyst, high yields and ease of separation of pure products.
文摘The condensation of benzaldehyde, urea, and ethyl acetoacetate according to the procedure described by Biginelli was investigated at the B3LYP/6-31G（d）, B3LYP/6-31 ＋G（d,p）, and B3LYP/6-311＋G（3df,2p）//B3LYP/6-31＋G（d,p） levels to explore the reaction mechanism. According to the mechanism proposed by Kappe, structures of five intermediates were optimized and four transition states were found. The calculation results proved that the mechanism proposed by Kappe is right.
文摘A new method for the synthesis of 1-methylimidazolium trifluoroacetate ([Hmi]Tfa), a protic ionic liquid (PIL), under ultrasonic irradiation has been developed. In addition, the product [Hmi]Tfa was successfully employed as solvent and catalyst in Biginelli reaction to prepare 3,4-dihydropyrimidinones (DHPMs) in high yield under mild reaction conditions.
文摘[Hmim][Tfa] was used as catalyst for the Biginelli reaction under microwave heating. Low catalyst loading, reduced reaction time and operational simplicity are the main highlights of this protocol. The proposed protocol was found active in the synthesis of 30 different biologically active compounds.
文摘A simple, green and highly efficient procedure for the Biginelli condensation reaction of aldehydes, β-ketoesters, urea or thiourea catalyzed by crushed garlic clove at ambient temperature is reported.
文摘4-Aryl-3, 4-dihydropyrimidinones were synthesized using microwave-assisted,solvent-free protocol of the Biginelli reaction. The simple method provides the title compounds in78%―95% yields by the reaction of aromatic aldehydes with ethyl acetoac-etate and urea/thiourea inthe presence of a catalytic amount of cone. HCl. Lewis acids, such as ZnCl_2, SnCl_2, FeCl_3·6H_2O,and CuCl_2·2H_2O, were also found to be efficient catalysts for the synthesis ofdihydropyrimidinones.
基金ProjectsupportedbytheNaturalScienceFoundationofShaanxiProvince (No .2 0 0 0H0 3)
文摘An efficient synthesis of 3,4-dihydropyrimidinones from aldehyde, β-ketoester and urea in ethanol using cobalt chloride hexahydrate or lanthanum chloride heptahydrate as acatalyst was described. Compared to the classical Biginelli reaction, this new method consistentlyhas the advantage of good yields (56%―99%) as well as short reaction tune (4―5 h).
文摘The effect of addition of poly（ethylene glycol）-400 （PEG-400） and carbon （0, 1, 2 and 3 wt%） as substrates were investigated systematically to get the desired phase of carbon-doped MoO3 material. The carbon source was prepared from the Acacia arabica plant wood. The resulting samples were calcined at 500 ℃. The effect of PEG-400 and carbon composite on the structure, particle size and morphology were investigated. The prepared samples were characterized by XRD, SEM-EDS and FT-IR techniques. The samples with PEG-400 and carbon ad- dition give better control of particle size and porosity. The prepared catalysts were tested for the synthesis of 3,4-dihydropyrimidones via the Biginelli-type condensation reaction. This new method consistently has the advan- tage of excellent yields （88%--93%） and short reaction times （1.5--3 h） than do classical Biginelli reaction conditions.
基金financial support by the National Natural Science Foundation of China (20972057, 20772043)the Excellent Scientist Foundation of Anhui Province, China (04046080)the Natural Science Foundation of Anhui Province's Higher Education, China (KJ2009B212Z)
文摘The immobilized nickel(II) on the organic-inorganic hybrid material was prepared and used as an effective catalyst for the Biginelli reaction.In the presence of the immobilized nickel catalyst,aromatic aldehydes reacted with ethyl acetoacetate and urea (or thiourea) smoothly to generate the corresponding Biginelli products in good to excellent yields without using any additive.The work-up procedure is very simple and practical.Furthermore,the silica-supported nickel(II) could be recovered and recycled for six consecutive trials without significant loss of its catalytic activity.
基金financial support from the National Natural Science Foundation of China (21002009, 21072093 & 20872051)the Doctoral Fund of Ministry of Education of China (20090091110017)+1 种基金Priority Academic Program Development of Jiangsu Higher Education Institutionsalso supported by the Fundamental Research Funds for the Central Universities (1107020526 & 1103020505)
文摘A series of novel supramolecular organocatalysts of hydroxyprolinamide based on the upper rim of calix[4]arene scaffold have been developed to catalyze enantioselective multi-component Biginelli reaction. Under the optimal conditions, the reactions occurred with moderate-to-excellent enantioselectivities (up to 98% ee). A plausible transition state constructed by the supra- molecular interaction of hydrogen bond and cation-π between catalysts and substrates has been proposed.
基金Supported by the National Natural Science Foundation of China（No.21002050）.
文摘A facile and efficient protocol for the synthesis of 3,4-dihydropyrimidones via one-pot Biginelli reaction in PEG1000-DAIL/toluene system was developed. PEG1000-DAIL/toluene mixture is a temperature-driven reversible b/phasic system, which promises the fully display of catalytic activity and simple recycle of PEGI0oo-DAIL. As a re- suit, PEG1000-DAIL/toluene mixture showed catalyst-medium double-duty in the Biginelli reaction and afforded cor- responding 3,4-dihydropyrimidones in excellent yields of activity was observed even after 10 recycling, runs. 80%---95% for 20 examples. No obvious loss of catalytic
基金supported by the National Natural Science Foundation of China(Nos.21901067,22171075)Starting Grant from the Ministry of Human Resource and Social Security of China(Q.L.)+1 种基金the NSFC of Guangxi Province(Nos.91122032,2017GXNSFDA198040)the BAGUI talent program(No.2019AC26001)。
文摘The low-cost CuBr-promoted domino Biginelli reaction among readily available ketones,salicylaldehyde derivatives and 3-amino-1,2,4-triazole was studied under solvothermal conditions,giving the novel bridged polyheterocycles bearing two or three stereocenters depending on the starting ketones.This multicomponent reaction proceeded with high diastereoselectivity(dr>20:1)based on a combined~1 H NMR,crystallographic and supercritical fluid chromatographic(SFC)analysis of the product.Time-dependent high-resolution mass spectrometry(HRMS)was performed to track the reaction process,and several key intermediates were identified,leading to the drawing of a plausible reaction mechanism.Density functional theory(DFT)calculation was supplemented,and two reaction pathways were differentiated.Moreover,in vitro antitumor activity was evaluated using HeLa and HepG2 cell lines,and two of these polyheterocycles demonstrated promising activities against HepG2 cells with EC50 down to 10μmol/L.Additionally,ESI-MS/MS studies on all the polyheterocycles suggest a common fragmentation pathway(loss of one molecule of amino-triazole)they shared,providing the first-hand fragmentation rules for future rapid structural identification of them.The multicomponent domino reaction presented here may offer prospects for future design of more efficient strategies to access medicinally important bridged polyheterocycles.
基金supported by the National Natural Science Foundation of China(21574073,21372033)
文摘Recently, the Biginelli reaction, one of the most famous multicomponent reactions, has been introduced into the polymer chemistry to highly efficiently synthesize some interesting functional polymers. In this mini-review, several applications of the Biginelli reaction in polymer chemistry have been summarized, including polycondensation, post-polymerization modification,one-pot synthesis of well-defined polymer, etc. Meanwhile, the utilization of the Biginelli reaction in material science and chemical biology, and the future development of the Biginelli reaction in polymer chemistry have also been discussed.
基金the University of Guilan Research Council for the partial support of this work
文摘A mild, simple and efficient procedure for the preparation of 3,4-dihydropyrimidin-2（1H）-ones and -thiones is described using N-sulfonic acid poly（4-vinylpyridinium） chloride （NSPVPC） as a heterogeneous and efficient catalyst under solvent-free conditions. Simple methodologies, easy work-up procedure, easy preparation of the catalyst, excellent yields and very short reaction times are among the other advantages of this work. Further, the catalyst can be reused and recovered for several times without significant decrease in its activity.
