Herein,we report a condition-controlled divergent synthesis of spiro indene-2,1'-isoindolinones and spiro isochroman-3,1'-isoindolinones through cobalt-catalyzed formal[4+1]and[4+1+1]spirocyclization of aromat...Herein,we report a condition-controlled divergent synthesis of spiro indene-2,1'-isoindolinones and spiro isochroman-3,1'-isoindolinones through cobalt-catalyzed formal[4+1]and[4+1+1]spirocyclization of aromatic amides with 2-diazo-1H-indene-1,3(2H)-dione.When the reaction is carried out under air in ethyl acetate,spiro indene-2,1'-isoindolinones are formed through Co(II)-catalyzed C—H/N—H[4+1]spirocyclization.When the reaction is run under O2 in CH3CN,on the other hand,spiro isochroman-3,1'-isoindolinones are generated through Baeyer-Villiger oxidation of the in situ formed spiro indene-2,1'-isoindolinones with O2 as a cheaper and environmental-friendly oxygen source.In general,these protocols have advantages such as using non-precious and earth-abundant metal catalyst,no extra additive,high efficiency and regioselectivity.A gram-scale synthesis and the removal of the directing group further highlight its utility.展开更多
The important synthetic precursor(Ⅲ), 1-(prop-2-yn-1-yl)-7,8-dihydro-1Hbenzo[d][1,3]thiazine-2,5(4H,6H)-dione(C(11)H(11)NO2S), was prepared through a three-component reaction, which was further transferre...The important synthetic precursor(Ⅲ), 1-(prop-2-yn-1-yl)-7,8-dihydro-1Hbenzo[d][1,3]thiazine-2,5(4H,6H)-dione(C(11)H(11)NO2S), was prepared through a three-component reaction, which was further transferred into cytotoxic triazoles by alkylation and "click" synthesis in satisfactory yields of 87%^95%. Their structures were characterized by IR, H-RESI-MS and NMR analysis. Meanwhile, the crystal of Ⅲ was obtained and determined by X-ray single-crystal diffraction. Crystal data: orthorhombic system, space group P212121, a = 5.189(4), b = 8.661(6), c = 23.498(17) A, V = 1056.2(13) A^3, Z = 4, F(000) = 464, Dc = 1.392 g/cm^3, μ =0.284 mm^-1, R = 0.0637 and wR = 0.1668 for 8182 independent reflections(R(int) = 0.1580) and 2166 observed ones(I 〉 2σ(I)).展开更多
A protocol for the synthesis of some 4-Aryl-1,3,4,6,7,8-hexahydroquinazolin-2,5(1H,6H)-diones (HHQs) was developed by means of a three-component condensation reaction of an aromatic aldehyde, 1,3-cylohexadione and ure...A protocol for the synthesis of some 4-Aryl-1,3,4,6,7,8-hexahydroquinazolin-2,5(1H,6H)-diones (HHQs) was developed by means of a three-component condensation reaction of an aromatic aldehyde, 1,3-cylohexadione and urea in the presence of K3AlF6 (Al2O3/KF) as catalyst. This reaction is carried out under different conditions including 1) solvent free;2) reflux in acetonitrile;3) reflux in ethanol;4) reflux in chloroform;and 5) reflux in water. In all conditions, the desired products are obtained in high yields after relatively short reaction times. Nevertheless, the reactions proceed faster and in higher yields when they were carried out in acetonitrile. This adopted protocol for some Biginelli-type products has offered the advantages of reusability of the catalyst, high yields and ease of separation of pure products. Furthermore, the catalyst is easily prepared, stabilized and efficiently used under reaction conditions.展开更多
The reaction of furan-2,3-diones with S-methylisothiosemicarbazide hydroiodide yielded novel 1,2,4- triazine-5(4H)-ones, and reaction of furan-2,3-diones with diaminomaleonitrile led to the formation of pyrazine-2,3...The reaction of furan-2,3-diones with S-methylisothiosemicarbazide hydroiodide yielded novel 1,2,4- triazine-5(4H)-ones, and reaction of furan-2,3-diones with diaminomaleonitrile led to the formation of pyrazine-2,3-dicarbonitrile derivatives, and the hydrolysis of these products led to the formation of more new pyrazine-2,3-dicarbonitrile derivatives. These compounds are potential herbicides and pesticides.展开更多
A series of compounds containing the 1H-pyrazino[1,2-a]quinoxaline-1,5(6H)-dione scaffold have been synthesized using a one-pot procedure under microwave irradiation. This new strategy allowed for the facile synthesis...A series of compounds containing the 1H-pyrazino[1,2-a]quinoxaline-1,5(6H)-dione scaffold have been synthesized using a one-pot procedure under microwave irradiation. This new strategy allowed for the facile synthesis of target compounds in good yields and could be readily applied to the construction of diverse libraries of compounds for high throughput screening in medicinal chemistry.展开更多
Agreen regioselective synthesis of some new and known 9-aryl-5,9-dihydropyrimido[4,5-d][l,2,4]triazolo[1,5-a]pyrimidine-6,8(4H,7H)-diones has been described via the microwave-assisted one-pot reaction of 3-amino-1H-...Agreen regioselective synthesis of some new and known 9-aryl-5,9-dihydropyrimido[4,5-d][l,2,4]triazolo[1,5-a]pyrimidine-6,8(4H,7H)-diones has been described via the microwave-assisted one-pot reaction of 3-amino-1H-1,2,4-triazoles,aromatic aldehydes and barbituric acids under solvent- and catalyst-free conditions.This operationally simple procedure is less laborious and provides a better scope than previously reported procedures.展开更多
基金the National Natural Science Foundation of China(22101075,U2004189)Central Plains Science and Technology Innovation Leader Project(224200510009)+1 种基金Postdoctoral Research Grant in Henan Province(202103085)Henan Key Laboratory of Organic Functional Molecules and Drug Innovation,and 111 Project(D17007)for financial support.
文摘Herein,we report a condition-controlled divergent synthesis of spiro indene-2,1'-isoindolinones and spiro isochroman-3,1'-isoindolinones through cobalt-catalyzed formal[4+1]and[4+1+1]spirocyclization of aromatic amides with 2-diazo-1H-indene-1,3(2H)-dione.When the reaction is carried out under air in ethyl acetate,spiro indene-2,1'-isoindolinones are formed through Co(II)-catalyzed C—H/N—H[4+1]spirocyclization.When the reaction is run under O2 in CH3CN,on the other hand,spiro isochroman-3,1'-isoindolinones are generated through Baeyer-Villiger oxidation of the in situ formed spiro indene-2,1'-isoindolinones with O2 as a cheaper and environmental-friendly oxygen source.In general,these protocols have advantages such as using non-precious and earth-abundant metal catalyst,no extra additive,high efficiency and regioselectivity.A gram-scale synthesis and the removal of the directing group further highlight its utility.
基金Supported by the National Natural Science Foundation of China(No.21272136)Scientific Foundation from graduate school(2015CX131)Youth Talent Development Foundation of China Three Gorges University
文摘The important synthetic precursor(Ⅲ), 1-(prop-2-yn-1-yl)-7,8-dihydro-1Hbenzo[d][1,3]thiazine-2,5(4H,6H)-dione(C(11)H(11)NO2S), was prepared through a three-component reaction, which was further transferred into cytotoxic triazoles by alkylation and "click" synthesis in satisfactory yields of 87%^95%. Their structures were characterized by IR, H-RESI-MS and NMR analysis. Meanwhile, the crystal of Ⅲ was obtained and determined by X-ray single-crystal diffraction. Crystal data: orthorhombic system, space group P212121, a = 5.189(4), b = 8.661(6), c = 23.498(17) A, V = 1056.2(13) A^3, Z = 4, F(000) = 464, Dc = 1.392 g/cm^3, μ =0.284 mm^-1, R = 0.0637 and wR = 0.1668 for 8182 independent reflections(R(int) = 0.1580) and 2166 observed ones(I 〉 2σ(I)).
文摘A protocol for the synthesis of some 4-Aryl-1,3,4,6,7,8-hexahydroquinazolin-2,5(1H,6H)-diones (HHQs) was developed by means of a three-component condensation reaction of an aromatic aldehyde, 1,3-cylohexadione and urea in the presence of K3AlF6 (Al2O3/KF) as catalyst. This reaction is carried out under different conditions including 1) solvent free;2) reflux in acetonitrile;3) reflux in ethanol;4) reflux in chloroform;and 5) reflux in water. In all conditions, the desired products are obtained in high yields after relatively short reaction times. Nevertheless, the reactions proceed faster and in higher yields when they were carried out in acetonitrile. This adopted protocol for some Biginelli-type products has offered the advantages of reusability of the catalyst, high yields and ease of separation of pure products. Furthermore, the catalyst is easily prepared, stabilized and efficiently used under reaction conditions.
基金financially supported by the Center of Research Projects of Bozok University (No. IFE 2011/46)
文摘The reaction of furan-2,3-diones with S-methylisothiosemicarbazide hydroiodide yielded novel 1,2,4- triazine-5(4H)-ones, and reaction of furan-2,3-diones with diaminomaleonitrile led to the formation of pyrazine-2,3-dicarbonitrile derivatives, and the hydrolysis of these products led to the formation of more new pyrazine-2,3-dicarbonitrile derivatives. These compounds are potential herbicides and pesticides.
基金supported by the Scientific Research Foundation of Chongqing University of Arts and Sciences(R2013XY01,R2013XY02)the Chongqing Science and Technology Commission(CSTC2013JCYJA50028)SRF for ROCS,SEM
文摘A series of compounds containing the 1H-pyrazino[1,2-a]quinoxaline-1,5(6H)-dione scaffold have been synthesized using a one-pot procedure under microwave irradiation. This new strategy allowed for the facile synthesis of target compounds in good yields and could be readily applied to the construction of diverse libraries of compounds for high throughput screening in medicinal chemistry.
文摘Agreen regioselective synthesis of some new and known 9-aryl-5,9-dihydropyrimido[4,5-d][l,2,4]triazolo[1,5-a]pyrimidine-6,8(4H,7H)-diones has been described via the microwave-assisted one-pot reaction of 3-amino-1H-1,2,4-triazoles,aromatic aldehydes and barbituric acids under solvent- and catalyst-free conditions.This operationally simple procedure is less laborious and provides a better scope than previously reported procedures.