Comprehensive Summary:The divergent synthesis of 2-quinolinones and indolin-3-ones through unprecedented Mo-catalyzed controllable carbonyl deoxygenative coupling and formal deoxygenative N-H insertion reactions was r...Comprehensive Summary:The divergent synthesis of 2-quinolinones and indolin-3-ones through unprecedented Mo-catalyzed controllable carbonyl deoxygenative coupling and formal deoxygenative N-H insertion reactions was reported.By simply changing the molybdenum catalytic conditions,both product categories were produced in generally good yields and with high chemoselectivities from the same starting materials.This strategy was robust,convenient and ready for the rapid construction of diverse product libraries.展开更多
The first HFIP-promoted catalyst-free cascade reactions for the synthesis of biologically relevant 3,3-di(indolyl)indolin-2-ones(27 examples,up to 98% yield) from readily available indoles and isatin derivatives are d...The first HFIP-promoted catalyst-free cascade reactions for the synthesis of biologically relevant 3,3-di(indolyl)indolin-2-ones(27 examples,up to 98% yield) from readily available indoles and isatin derivatives are described.This protocol shows well tolerance of different functional groups and features mild reaction conditions such as short reaction time(~1 h),no usage of catalyst,easy operation and product isolation.Of particular intere st is the formation of two C-C bonds and one all-carbon quaternary center.This protocol could serve as an alternative strategy to synthesize biologically important 3,3-di(indolyl)indolin-2-ones for biological testing.展开更多
A novel series of compounds combining indolin-2-one and quinazolin-4（3H）-one moiety via a carbon-carbon double bond were synthesized by aldol-condensation of 2-methylquinazolin-4（3H）-one-6-carbaldehyde with variou...A novel series of compounds combining indolin-2-one and quinazolin-4（3H）-one moiety via a carbon-carbon double bond were synthesized by aldol-condensation of 2-methylquinazolin-4（3H）-one-6-carbaldehyde with various indolin-2-ones. The synthesized compounds were evaluated for their cytotoxic activity against five human cancer cell lines, namely, A549, MCF-7, HeLa, HT-29 and HCT-116. We found that compound 5e with two bromine atoms at the 5- and 7-positions of the indolin-2-one ring was most potent, which inhibited proliferation of five cancer cell lines in the range of 32.0%-62.3% at a concentration of 50 p,M. Our results further indicate that the connection of 5,7-dibromoindolin-2-one and 2-methylquinazolin- 4（3H）-one moiety with a carbon-carbon double bond is essential for compound 5e to exert cytotoxicity.展开更多
Heteropoly acids efficiently catalyzed the cyclocondensation reaction of anthranilamide with aldehydes in water at ambient temperature and afforded the corresponding 2,3-dihydro-4（1H）-quinazolinones compounds in goo...Heteropoly acids efficiently catalyzed the cyclocondensation reaction of anthranilamide with aldehydes in water at ambient temperature and afforded the corresponding 2,3-dihydro-4（1H）-quinazolinones compounds in good to excellent yields.This method provides mild reaction conditions and clean reaction profiles,using a small quantity of catalyst and a simple workup procedure.展开更多
A new approach to the facile synthesis of 2-substituted-quinazolin-4（3H）-ones and its derivatives using the condensation reaction of substituted 2-aminobenzamide and orthoesters is reported.
A series of 2,3-dihydroquinazolin-4（1H）-ones have been synthesized in good to excellent yields through direct cyclocondensation of anthranilamide and aryl aldehydes or ketones in water or methanol under mild conditi...A series of 2,3-dihydroquinazolin-4（1H）-ones have been synthesized in good to excellent yields through direct cyclocondensation of anthranilamide and aryl aldehydes or ketones in water or methanol under mild conditions.The reaction was efficiently promoted by 10 mol%sulfamic acid（SA,H_2NSO_3H） and the catalyst could be recovered easily after the reactions and reused without evident loss of reactivity.展开更多
Melamine trisulfonic acid（MTSA） can be used as an efficient and recyclable catalyst for the promotion of the synthesis of 3,4- dihydropyrimidin-2（1H）-ones/thiones（DHPMs） in the absence of solvent.All reactions w...Melamine trisulfonic acid（MTSA） can be used as an efficient and recyclable catalyst for the promotion of the synthesis of 3,4- dihydropyrimidin-2（1H）-ones/thiones（DHPMs） in the absence of solvent.All reactions were performed at 80℃in good to high yields.展开更多
Two compounds,3-oxo-N-o-tolylbenzo[d]isothiazole-2（3H）-carboxamide （1） and N-（2-methoxyphenyl）-3-oxobenzo[d]isothiazole-2（3H）-carboxamide （2）,were synthesized from the initial compound benzo[d]isothiazol-3...Two compounds,3-oxo-N-o-tolylbenzo[d]isothiazole-2（3H）-carboxamide （1） and N-（2-methoxyphenyl）-3-oxobenzo[d]isothiazole-2（3H）-carboxamide （2）,were synthesized from the initial compound benzo[d]isothiazol-3（2H）-one （BIT） and characterized by 1 H NMR,IR and elemental analysis,respectively.The single crystals of compounds 1 and 2 were obtained and determined by X-ray diffraction analysis.The preliminary results of biological activity experiment show that some of the title compounds exhibited a favorable antimicrobial activity.展开更多
2,3-Dihydroquinazolin-4（1H）-ones have been synthesized in the high to excellent yields via condensation of 2-aminobenzamide with aldehydes and ketones in the presence of catalytic amount of ZrCl_4 in EtOH at room te...2,3-Dihydroquinazolin-4（1H）-ones have been synthesized in the high to excellent yields via condensation of 2-aminobenzamide with aldehydes and ketones in the presence of catalytic amount of ZrCl_4 in EtOH at room temperature.Mild reaction conditions, clean reaction media,simple workup and easy purification are advantages of this methodology.展开更多
An efficient method for the synthesis of benzo[b]benzofurano[2,3-e][1,6]naphthyridine-8-one derivatives has been developed via Pictet-Spengler reaction of 4-（3-aminobenzofuran-2-yl）quinoline-2-ones,which could be ob...An efficient method for the synthesis of benzo[b]benzofurano[2,3-e][1,6]naphthyridine-8-one derivatives has been developed via Pictet-Spengler reaction of 4-（3-aminobenzofuran-2-yl）quinoline-2-ones,which could be obtained from alkylation of 4-bromomethylquinoline-2-ones with salicylonitrile and subsequent Thorpe-Ziegier isomerization,with aromatic aldehydes under p-TsOH as catalyst in good yields.展开更多
A facile one-pot synthesis of 3,4,5-substituted furan-2（5H）-one derivatives from a three-component reaction of aniline derivatives, dialkylacetylenedicarboxylates and aromatic aldehydes under mild conditions using t...A facile one-pot synthesis of 3,4,5-substituted furan-2（5H）-one derivatives from a three-component reaction of aniline derivatives, dialkylacetylenedicarboxylates and aromatic aldehydes under mild conditions using tetra-n-butylammonium bisulfate as a catalyst has been developed.展开更多
A wide range of mono-and disubstituted 2,3-dihydroquinazolin-4（1H）-ones were obtained in high yields by condensation of isatoic anhydride,aldehydes with ammonium salts or primary amines in the presence of strontium ...A wide range of mono-and disubstituted 2,3-dihydroquinazolin-4（1H）-ones were obtained in high yields by condensation of isatoic anhydride,aldehydes with ammonium salts or primary amines in the presence of strontium chloride in aqueous ethanol under reflux.展开更多
A new one-pot neat synthesis of some 5-aryl-2,4-dihydro-3H- 1,2,4-triazol-3-ones through cyclocondensation of ethyl carbazate with aryl nitriles catalyzed by DMAP as an efficient and basic nucleophilic catalyst is des...A new one-pot neat synthesis of some 5-aryl-2,4-dihydro-3H- 1,2,4-triazol-3-ones through cyclocondensation of ethyl carbazate with aryl nitriles catalyzed by DMAP as an efficient and basic nucleophilic catalyst is described.展开更多
Silica-supported tin chloride and titanium tetrachloride were prepared by the reaction of tin chloride and titanium tetrachloride with activated silica gel in refluxing toluene.These solid acids have been employed as ...Silica-supported tin chloride and titanium tetrachloride were prepared by the reaction of tin chloride and titanium tetrachloride with activated silica gel in refluxing toluene.These solid acids have been employed as the catalysts for the synthesis of bisdihydropyrimidin -2(1H)-ones from aromatic dialdehydes,1,3-dicarbonyl compounds and urea at 90℃under solvent-free conditions.展开更多
Vitamin B12 was applied as catalyst for the one-pot three-component synthesis of 3,4,5-trisubstituted furan-2（5H）-ones from the condensation between aldehydes, amines and dialkylacetylendicarboxylates at ambient tem...Vitamin B12 was applied as catalyst for the one-pot three-component synthesis of 3,4,5-trisubstituted furan-2（5H）-ones from the condensation between aldehydes, amines and dialkylacetylendicarboxylates at ambient temperature in Et OH. In addition, N-aryl-3-aminodihydropyrrol-2-one-4-carboxylates were synthesised using mentioned catalyst at ambient temperature in Et OH from condensation between formaldehyde, amines, and dialkylacetylenedicarboxylates. This methodology has number of advantages such as： use of green and nonhazardous catalyst, clean work up, short reaction times,high yields and no need to column chromatography.展开更多
A series of E and Z-isomers of 3-（4＇-substituted benzylidene）-indolin-2-one derivatives were synthesized and separated. Based on their 1H NMR characterization, an unusual counterintuitive deshielding phenomenon for...A series of E and Z-isomers of 3-（4＇-substituted benzylidene）-indolin-2-one derivatives were synthesized and separated. Based on their 1H NMR characterization, an unusual counterintuitive deshielding phenomenon for the protons presenting in the shielding zone of phenyl ring was observed and analyzed for the first time.展开更多
Alkylamino-5, 6, 7, 8-tetrahydrobenzothieno [2, 3-d] pyrimidin-4(3H)-ones 7 weresynthesized by a new selective synthetic method, which includes aza-Wittig reaction of imino-phosphorane 4 with aromatic isocynate to giv...Alkylamino-5, 6, 7, 8-tetrahydrobenzothieno [2, 3-d] pyrimidin-4(3H)-ones 7 weresynthesized by a new selective synthetic method, which includes aza-Wittig reaction of imino-phosphorane 4 with aromatic isocynate to give carbodiimide 5 and subsequent reaction of 5 withvarious aliphatic primary amine in the presence of EtO-Na+.展开更多
An environmentally benign aqueous protocol for the synthesis of 3,4-dihydropyrimidin-2-（ 1 H）-ones and thiones promoted by a green catalyst, silica gel-supported L-pyrrolidine-2-carboxylic acid-4-hydrogen sulfate, h...An environmentally benign aqueous protocol for the synthesis of 3,4-dihydropyrimidin-2-（ 1 H）-ones and thiones promoted by a green catalyst, silica gel-supported L-pyrrolidine-2-carboxylic acid-4-hydrogen sulfate, has been developed. The use of nontoxic, thermally stable and inexpensive amino acid catalyst makes the process simple with minimal amount of chemical waste. Compared with classical Biginelli reaction conditions, this new method has the advantages of high yields and simple workup procedures.展开更多
An efficient method for the synthesis of novel benzo[b]pyrido[3＇,2＇：4,5]thieno[2,3-e][l,6]naphthyridine-8-one derivatives has been developed using a Pictet-Spengler reaction between 4-（3-aminothieno[2,3-b]pyridin-...An efficient method for the synthesis of novel benzo[b]pyrido[3＇,2＇：4,5]thieno[2,3-e][l,6]naphthyridine-8-one derivatives has been developed using a Pictet-Spengler reaction between 4-（3-aminothieno[2,3-b]pyridin-2-yl）quinoline-2-ones,which could be obtained from the alkylation of4-bromomethylquinoline-2-ones with 3-cyanopyridine-2-thione followed by a Thorpe-Ziegler isomerization,and aromatic aldehydes under p-TsOH as catalysis in good yields.展开更多
An efficient ultrasound-assisted preparation of a series of novel 4-aryl-3-methyl-4,5-dihydro-l//-pyrazolo[34-b]pyridin-6（7H）ones via the reaction of 5-amino-3-methyl-1H-pyrazole,Meldrum＇s acid and various arylalde...An efficient ultrasound-assisted preparation of a series of novel 4-aryl-3-methyl-4,5-dihydro-l//-pyrazolo[34-b]pyridin-6（7H）ones via the reaction of 5-amino-3-methyl-1H-pyrazole,Meldrum＇s acid and various arylaldehydes using one-pot three-component approach is described.This rapid method produced the products in short reaction times（3-4 min） and excellent yields（87-95%）.展开更多
基金financial support from the National Key R&D Program of China(2021YFA1502500)the National Natural Science Foundation of china(22171236 and 22371238).
文摘Comprehensive Summary:The divergent synthesis of 2-quinolinones and indolin-3-ones through unprecedented Mo-catalyzed controllable carbonyl deoxygenative coupling and formal deoxygenative N-H insertion reactions was reported.By simply changing the molybdenum catalytic conditions,both product categories were produced in generally good yields and with high chemoselectivities from the same starting materials.This strategy was robust,convenient and ready for the rapid construction of diverse product libraries.
基金supported by the National Natural Science Foundation of China(Nos.81773562,81703326 and 81973177)The Open Project of State Key Laboratory of Natural Medicines(No.SKLNMKF202005)China Postdoctoral Science Foundation(Nos.2018M630840 and 2019T120641)。
文摘The first HFIP-promoted catalyst-free cascade reactions for the synthesis of biologically relevant 3,3-di(indolyl)indolin-2-ones(27 examples,up to 98% yield) from readily available indoles and isatin derivatives are described.This protocol shows well tolerance of different functional groups and features mild reaction conditions such as short reaction time(~1 h),no usage of catalyst,easy operation and product isolation.Of particular intere st is the formation of two C-C bonds and one all-carbon quaternary center.This protocol could serve as an alternative strategy to synthesize biologically important 3,3-di(indolyl)indolin-2-ones for biological testing.
基金National Natural Science Foundation of China (Grant No.20972099,31130017)Beijing Municipal Commission of Education (Grant No.KZ201210028035)+1 种基金Scientific Research Base Development Program of the Beijing Municipal Commission of Educationthe 973 Project (Grant No.2013CB911000)
文摘A novel series of compounds combining indolin-2-one and quinazolin-4（3H）-one moiety via a carbon-carbon double bond were synthesized by aldol-condensation of 2-methylquinazolin-4（3H）-one-6-carbaldehyde with various indolin-2-ones. The synthesized compounds were evaluated for their cytotoxic activity against five human cancer cell lines, namely, A549, MCF-7, HeLa, HT-29 and HCT-116. We found that compound 5e with two bromine atoms at the 5- and 7-positions of the indolin-2-one ring was most potent, which inhibited proliferation of five cancer cell lines in the range of 32.0%-62.3% at a concentration of 50 p,M. Our results further indicate that the connection of 5,7-dibromoindolin-2-one and 2-methylquinazolin- 4（3H）-one moiety with a carbon-carbon double bond is essential for compound 5e to exert cytotoxicity.
基金the financial support of Key Laboratory of Resources and Environment Chemistry of West China(No.XZ0704).
文摘Heteropoly acids efficiently catalyzed the cyclocondensation reaction of anthranilamide with aldehydes in water at ambient temperature and afforded the corresponding 2,3-dihydro-4（1H）-quinazolinones compounds in good to excellent yields.This method provides mild reaction conditions and clean reaction profiles,using a small quantity of catalyst and a simple workup procedure.
基金the Natural Science Foundation of China(Nos.U0832005,90813011,20772159,30801436)the Ministry of Education of the People's Republic of China(No.200805581163)+1 种基金the Guangdong Natural Science Foundation(No.8451008901000214)the Science Foundation of Guangzhou(No.2009A1-E011-6)for financial support of this study.
文摘A new approach to the facile synthesis of 2-substituted-quinazolin-4（3H）-ones and its derivatives using the condensation reaction of substituted 2-aminobenzamide and orthoesters is reported.
文摘A series of 2,3-dihydroquinazolin-4（1H）-ones have been synthesized in good to excellent yields through direct cyclocondensation of anthranilamide and aryl aldehydes or ketones in water or methanol under mild conditions.The reaction was efficiently promoted by 10 mol%sulfamic acid（SA,H_2NSO_3H） and the catalyst could be recovered easily after the reactions and reused without evident loss of reactivity.
基金the University of Guilan Research Council for the partial support of this work
文摘Melamine trisulfonic acid（MTSA） can be used as an efficient and recyclable catalyst for the promotion of the synthesis of 3,4- dihydropyrimidin-2（1H）-ones/thiones（DHPMs） in the absence of solvent.All reactions were performed at 80℃in good to high yields.
基金Supported by the National Natural Science Foundation of China (No. 20962007)the Creative Talents Plan of Hainan University 211 Project
文摘Two compounds,3-oxo-N-o-tolylbenzo[d]isothiazole-2（3H）-carboxamide （1） and N-（2-methoxyphenyl）-3-oxobenzo[d]isothiazole-2（3H）-carboxamide （2）,were synthesized from the initial compound benzo[d]isothiazol-3（2H）-one （BIT） and characterized by 1 H NMR,IR and elemental analysis,respectively.The single crystals of compounds 1 and 2 were obtained and determined by X-ray diffraction analysis.The preliminary results of biological activity experiment show that some of the title compounds exhibited a favorable antimicrobial activity.
文摘2,3-Dihydroquinazolin-4（1H）-ones have been synthesized in the high to excellent yields via condensation of 2-aminobenzamide with aldehydes and ketones in the presence of catalytic amount of ZrCl_4 in EtOH at room temperature.Mild reaction conditions, clean reaction media,simple workup and easy purification are advantages of this methodology.
基金financial support from the Science and Technology Department of Liaoning Province(No.2011220022)
文摘An efficient method for the synthesis of benzo[b]benzofurano[2,3-e][1,6]naphthyridine-8-one derivatives has been developed via Pictet-Spengler reaction of 4-（3-aminobenzofuran-2-yl）quinoline-2-ones,which could be obtained from alkylation of 4-bromomethylquinoline-2-ones with salicylonitrile and subsequent Thorpe-Ziegier isomerization,with aromatic aldehydes under p-TsOH as catalyst in good yields.
基金fnancial support from the Research Council of the University of Sistan and Baluchestan
文摘A facile one-pot synthesis of 3,4,5-substituted furan-2（5H）-one derivatives from a three-component reaction of aniline derivatives, dialkylacetylenedicarboxylates and aromatic aldehydes under mild conditions using tetra-n-butylammonium bisulfate as a catalyst has been developed.
文摘A wide range of mono-and disubstituted 2,3-dihydroquinazolin-4（1H）-ones were obtained in high yields by condensation of isatoic anhydride,aldehydes with ammonium salts or primary amines in the presence of strontium chloride in aqueous ethanol under reflux.
文摘A new one-pot neat synthesis of some 5-aryl-2,4-dihydro-3H- 1,2,4-triazol-3-ones through cyclocondensation of ethyl carbazate with aryl nitriles catalyzed by DMAP as an efficient and basic nucleophilic catalyst is described.
文摘Silica-supported tin chloride and titanium tetrachloride were prepared by the reaction of tin chloride and titanium tetrachloride with activated silica gel in refluxing toluene.These solid acids have been employed as the catalysts for the synthesis of bisdihydropyrimidin -2(1H)-ones from aromatic dialdehydes,1,3-dicarbonyl compounds and urea at 90℃under solvent-free conditions.
基金financial support from the Research Council of the University of Sistan and Baluchestan,Zahedan, Iran
文摘Vitamin B12 was applied as catalyst for the one-pot three-component synthesis of 3,4,5-trisubstituted furan-2（5H）-ones from the condensation between aldehydes, amines and dialkylacetylendicarboxylates at ambient temperature in Et OH. In addition, N-aryl-3-aminodihydropyrrol-2-one-4-carboxylates were synthesised using mentioned catalyst at ambient temperature in Et OH from condensation between formaldehyde, amines, and dialkylacetylenedicarboxylates. This methodology has number of advantages such as： use of green and nonhazardous catalyst, clean work up, short reaction times,high yields and no need to column chromatography.
基金National Natural Science Foundation of China(Grant No.21172008 and 21372015)
文摘A series of E and Z-isomers of 3-（4＇-substituted benzylidene）-indolin-2-one derivatives were synthesized and separated. Based on their 1H NMR characterization, an unusual counterintuitive deshielding phenomenon for the protons presenting in the shielding zone of phenyl ring was observed and analyzed for the first time.
基金We gratefully acknowledge financial support of this work by the National Key Project for Basic Research(2003CB114400,2003CB114406)the National Natural Science Foundation of China(Project No.20102001).
文摘Alkylamino-5, 6, 7, 8-tetrahydrobenzothieno [2, 3-d] pyrimidin-4(3H)-ones 7 weresynthesized by a new selective synthetic method, which includes aza-Wittig reaction of imino-phosphorane 4 with aromatic isocynate to give carbodiimide 5 and subsequent reaction of 5 withvarious aliphatic primary amine in the presence of EtO-Na+.
基金Financial support to this work by the Ilam University,Ilam,Iran is gratefully acknowledged
文摘An environmentally benign aqueous protocol for the synthesis of 3,4-dihydropyrimidin-2-（ 1 H）-ones and thiones promoted by a green catalyst, silica gel-supported L-pyrrolidine-2-carboxylic acid-4-hydrogen sulfate, has been developed. The use of nontoxic, thermally stable and inexpensive amino acid catalyst makes the process simple with minimal amount of chemical waste. Compared with classical Biginelli reaction conditions, this new method has the advantages of high yields and simple workup procedures.
文摘An efficient method for the synthesis of novel benzo[b]pyrido[3＇,2＇：4,5]thieno[2,3-e][l,6]naphthyridine-8-one derivatives has been developed using a Pictet-Spengler reaction between 4-（3-aminothieno[2,3-b]pyridin-2-yl）quinoline-2-ones,which could be obtained from the alkylation of4-bromomethylquinoline-2-ones with 3-cyanopyridine-2-thione followed by a Thorpe-Ziegler isomerization,and aromatic aldehydes under p-TsOH as catalysis in good yields.
基金Financial support from the Research Council of University of Guilan is sincerely acknowledged
文摘An efficient ultrasound-assisted preparation of a series of novel 4-aryl-3-methyl-4,5-dihydro-l//-pyrazolo[34-b]pyridin-6（7H）ones via the reaction of 5-amino-3-methyl-1H-pyrazole,Meldrum＇s acid and various arylaldehydes using one-pot three-component approach is described.This rapid method produced the products in short reaction times（3-4 min） and excellent yields（87-95%）.
