Synthesis of tetrahydrofuran and tetrahydropyran derivatives catalyzed by tungstophosphoric acid （H3PW12040） were conveniently performed with high yield from the corresponding unsaturated alcohols in ionic liquid. S...Synthesis of tetrahydrofuran and tetrahydropyran derivatives catalyzed by tungstophosphoric acid （H3PW12040） were conveniently performed with high yield from the corresponding unsaturated alcohols in ionic liquid. Sufuric acid （H2SO4）, trifluoromathanesulfonic acid （TfOH） and p-toluenesulfonic acid （TsOH） were also explored for preparing these products in ionic liquid. The catalysts and ionic liquid can be easily recovered and reused.展开更多
Piperidine-4-ones and tetrahydropyrane-4-ones are important precursors for the synthesis of functionally substituted piperidines and tetrahydropyranes. In this study, the condensation of hexa-2, 4-diene and 2-methyl-p...Piperidine-4-ones and tetrahydropyrane-4-ones are important precursors for the synthesis of functionally substituted piperidines and tetrahydropyranes. In this study, the condensation of hexa-2, 4-diene and 2-methyl-penta-2, 4-diene with formaldehyde （reaction of oxymethylation） was investigated. The functionally substituted derivatives of piperidine and tetrahydropyrane were synthesized. The comparison of oxymethylation of dienes and 1-alkenes was showed, which indicates that the highest yield of tetrahydropyrane derivatives was achieved with 1-alkenes. This study provided theoretical basis for the synthesis of piperidine and tetrahydropyrane derivatives.展开更多
In dichloromethane, the nucleophilic addition of alcohols or phenols to 3,4-dihydro-2H-pyran (DHP) was cata-lyzed effectively by gallium triiodide which was generated in situ by the reaction of gallium metal and iodin...In dichloromethane, the nucleophilic addition of alcohols or phenols to 3,4-dihydro-2H-pyran (DHP) was cata-lyzed effectively by gallium triiodide which was generated in situ by the reaction of gallium metal and iodine to give the corresponding tetrahydropyranyl acetals in good to excellent yields.展开更多
By investigating the effect of the amount of water, the ratio of aldehyde and allyl- bromide, and the reaction temperature on the transformation, 2,4,6-trisubstituted tetrahydro- pyrans are synthesized by a novel tand...By investigating the effect of the amount of water, the ratio of aldehyde and allyl- bromide, and the reaction temperature on the transformation, 2,4,6-trisubstituted tetrahydro- pyrans are synthesized by a novel tandem Barbier-Prins-cyclization reaction in the presence of micro-amount of water under mild conditions. The experiment is easy to perform without the need to exclude moisture or air. The reaction is atomic economical and environmentally benign.展开更多
An unprecedented protocol has been developed for the efficient synthesis of substituted tetrahydropyrans via a bismuth-promoted Prins cyclization of imines with homoallyl alcohols.In the presence of 40 mol%BiCl_(3),a ...An unprecedented protocol has been developed for the efficient synthesis of substituted tetrahydropyrans via a bismuth-promoted Prins cyclization of imines with homoallyl alcohols.In the presence of 40 mol%BiCl_(3),a wide variety of imines react smoothly with homoallyl alcohols at room temperature to give the corresponding 4-chlorotetrahydropyran derivatives in good to excellent yields.展开更多
An efficient asymmetric and enantio-swithchable organocatalytic[3+3]annulation reaction using MBH-2-naphthoates of nitroalkenes and 4-hydroxyquinolin-2(1H)-ones has been developed.Densely substituted tetrahydropyrano[...An efficient asymmetric and enantio-swithchable organocatalytic[3+3]annulation reaction using MBH-2-naphthoates of nitroalkenes and 4-hydroxyquinolin-2(1H)-ones has been developed.Densely substituted tetrahydropyrano[3,2-c]qui noli nones scaffolds with two adjacent stereogenic centers are obtained with high yield(up to 95%yield)and good stereoselectivities(up to>20:1 dr and 96%ee)in an enantio-switchable manner.Furthermore,gram scale synthesis was achieved and the nitro group could easily transform into an amino group without any appreciable loss in the diastereo-and enantioselectivity.展开更多
Several ZSM-5 derived micro-mesoporous catalysts were investigated in Prins cyclisation of (-)-isopulegol with benzaldehyde acting as a reactant and a solvent for production of heterocyclic oxygen containing 2H-chrome...Several ZSM-5 derived micro-mesoporous catalysts were investigated in Prins cyclisation of (-)-isopulegol with benzaldehyde acting as a reactant and a solvent for production of heterocyclic oxygen containing 2H-chromene derivatives including the tetrahydropyran structure and exhibiting biological activity. The investigated catalysts were characterized by nitrogen adsorption, ammonia temperature programmed desorption, adsorption-desorption of pyridine and 2,6-di-tert- butylpyridine with Fourier transform infrared spectroscopic control. For the Prins reaction performed at 70℃, the highest yield of the desired product, equal to 67% at complete conversion of (-)-isopulegol, was obtained over a micro-mesoporous catalyst containing an optimum amount of strong acid sites and mesopores, being 12 fold larger than the size of the desired product.展开更多
文摘Synthesis of tetrahydrofuran and tetrahydropyran derivatives catalyzed by tungstophosphoric acid （H3PW12040） were conveniently performed with high yield from the corresponding unsaturated alcohols in ionic liquid. Sufuric acid （H2SO4）, trifluoromathanesulfonic acid （TfOH） and p-toluenesulfonic acid （TsOH） were also explored for preparing these products in ionic liquid. The catalysts and ionic liquid can be easily recovered and reused.
文摘Piperidine-4-ones and tetrahydropyrane-4-ones are important precursors for the synthesis of functionally substituted piperidines and tetrahydropyranes. In this study, the condensation of hexa-2, 4-diene and 2-methyl-penta-2, 4-diene with formaldehyde （reaction of oxymethylation） was investigated. The functionally substituted derivatives of piperidine and tetrahydropyrane were synthesized. The comparison of oxymethylation of dienes and 1-alkenes was showed, which indicates that the highest yield of tetrahydropyrane derivatives was achieved with 1-alkenes. This study provided theoretical basis for the synthesis of piperidine and tetrahydropyrane derivatives.
基金Project supported by the Natural Science Foundation of the Education Department of Jiangsu province (No. 03KJD150109).
文摘In dichloromethane, the nucleophilic addition of alcohols or phenols to 3,4-dihydro-2H-pyran (DHP) was cata-lyzed effectively by gallium triiodide which was generated in situ by the reaction of gallium metal and iodine to give the corresponding tetrahydropyranyl acetals in good to excellent yields.
基金the Key Foundation of the Ministry of Education of China National Natural Science Foundation of China(Grant No.20372033).
文摘By investigating the effect of the amount of water, the ratio of aldehyde and allyl- bromide, and the reaction temperature on the transformation, 2,4,6-trisubstituted tetrahydro- pyrans are synthesized by a novel tandem Barbier-Prins-cyclization reaction in the presence of micro-amount of water under mild conditions. The experiment is easy to perform without the need to exclude moisture or air. The reaction is atomic economical and environmentally benign.
基金We are grateful for the financial support from the National Natural Science Foundation of China(No.21202154)Nanjing Institute of Technology Fund for Talents(No.YKJ201329)Nanjing Institute of Technology and the University of Science and Technology of China.
文摘An unprecedented protocol has been developed for the efficient synthesis of substituted tetrahydropyrans via a bismuth-promoted Prins cyclization of imines with homoallyl alcohols.In the presence of 40 mol%BiCl_(3),a wide variety of imines react smoothly with homoallyl alcohols at room temperature to give the corresponding 4-chlorotetrahydropyran derivatives in good to excellent yields.
基金financial support from the National Natural Science Foundation of China(No.81602972)Guangdong Natural Science Funds for Distinguished Young Scholar(No.2018B030306017)Guangdong Province Universities and Colleges Pearl River Scholar Funded Scheme(2018)。
文摘An efficient asymmetric and enantio-swithchable organocatalytic[3+3]annulation reaction using MBH-2-naphthoates of nitroalkenes and 4-hydroxyquinolin-2(1H)-ones has been developed.Densely substituted tetrahydropyrano[3,2-c]qui noli nones scaffolds with two adjacent stereogenic centers are obtained with high yield(up to 95%yield)and good stereoselectivities(up to>20:1 dr and 96%ee)in an enantio-switchable manner.Furthermore,gram scale synthesis was achieved and the nitro group could easily transform into an amino group without any appreciable loss in the diastereo-and enantioselectivity.
文摘Several ZSM-5 derived micro-mesoporous catalysts were investigated in Prins cyclisation of (-)-isopulegol with benzaldehyde acting as a reactant and a solvent for production of heterocyclic oxygen containing 2H-chromene derivatives including the tetrahydropyran structure and exhibiting biological activity. The investigated catalysts were characterized by nitrogen adsorption, ammonia temperature programmed desorption, adsorption-desorption of pyridine and 2,6-di-tert- butylpyridine with Fourier transform infrared spectroscopic control. For the Prins reaction performed at 70℃, the highest yield of the desired product, equal to 67% at complete conversion of (-)-isopulegol, was obtained over a micro-mesoporous catalyst containing an optimum amount of strong acid sites and mesopores, being 12 fold larger than the size of the desired product.
