Sulfanilic acid has been found to be an efficient catalyst for the synthesis of 1,5-benzodiazepines from o-phenylenediamine and ketones. This method is simple, effective and environmentally friendly and gives better y...Sulfanilic acid has been found to be an efficient catalyst for the synthesis of 1,5-benzodiazepines from o-phenylenediamine and ketones. This method is simple, effective and environmentally friendly and gives better yields.展开更多
A general, mild and efficient protocol for the synthesis of ethyl 4-methyl-2-（thiophen）-2,5-dihydro-1,5- benzodiazepine-3-carboxylate is achieved for first time using H3PMo12O40 in ethanol at 0 ℃ by a one- pot, th...A general, mild and efficient protocol for the synthesis of ethyl 4-methyl-2-（thiophen）-2,5-dihydro-1,5- benzodiazepine-3-carboxylate is achieved for first time using H3PMo12O40 in ethanol at 0 ℃ by a one- pot, three-component condensation of various thiophene aldehydes, substituted o-phenylenediamines and ethyl acetoacetate. Compared with the conventional synthesis method, this procedure has the advantages of convenient operation, excellent yields, and environmentally benign. A plausible formation mechanism has been proposed. The structure of the products is characterized by1H NMR, IR, MS and elemental analysis.展开更多
MgBr2 performs as a novel catalyst for the synthesis of various 1,5-benzodiazepine derivatives from wide range of substituted o- phenylenediamines and various ketones in good to excellent isolated yields （93-98%） us...MgBr2 performs as a novel catalyst for the synthesis of various 1,5-benzodiazepine derivatives from wide range of substituted o- phenylenediamines and various ketones in good to excellent isolated yields （93-98%） using water as solvent at ambient temperature. Several solvents were examined for this reaction; however, in terms of reaction yield and time, water was found to be the optimum solvent. The remarkable advantages offered by this method are easily and inexpensive available catalyst, simple procedure, mild conditions, much faster （40-60 man） reactions and good to excellent yields of products.展开更多
Borax/phosphorous oxychloride （BPO） efficiently catalyzes the preparation of 1,5-benzodiazepine derivatives of o-phenylenediamines and ketones in solvent-free and solution conditions. The reaction proceeds efficient...Borax/phosphorous oxychloride （BPO） efficiently catalyzes the preparation of 1,5-benzodiazepine derivatives of o-phenylenediamines and ketones in solvent-free and solution conditions. The reaction proceeds efficiently under ambient conditions giving excellent yields of the products. This new protocol allows the recycling of catalyst with no loss in its potency.展开更多
Three kinds of products have been separated from the reaction mixtures of 1,2-dihydro-2, 4-disubstituted-1,5-benzodiazepine with: CCI_2.Besides the addition products of: CCI_2 to C=N.the inserted products of: CCI_2 to...Three kinds of products have been separated from the reaction mixtures of 1,2-dihydro-2, 4-disubstituted-1,5-benzodiazepine with: CCI_2.Besides the addition products of: CCI_2 to C=N.the inserted products of: CCI_2 to N-H and C-H single bonds were obtained, too.展开更多
The title compound C18H16N4O3 （Mr = 336.35） has been synthesized and characterized by elemental analysis and single-crystal X-ray diffraction. The Schiff base compound is a derivative of 4-aminoantipyrine. As expect...The title compound C18H16N4O3 （Mr = 336.35） has been synthesized and characterized by elemental analysis and single-crystal X-ray diffraction. The Schiff base compound is a derivative of 4-aminoantipyrine. As expected, the molecular structure adopts a trans configuration about the central C=N double bond. It crystallizes in orthorhombic, space group P2dc with a = 7.632（1）, b = 7.816（1）, c = 28.082（5） A,β = 96.18（1）°, V= 1665.48（51） A^3, Z= 4, Dc = 1.341 g/cm^3, F（000） = 704,μ = 0.094 mm^-1, the final R = 0.0448 and wR = 0.1058. Of the total 3748 collections, 3105 were unique. In the molecule there exist two different planes of pyrazoline and C（11）-C（16） phenyl ring, which are approximately coplanar （r.m.s. de deviation from the combined mean plane is 0.03 A） with the dihedral angle between them of 9.8%.展开更多
A novel benzo [ 1,5] oxazepin-4-one skeleton compound and its four derivatives were synthesized effectively from 1,5-difluoro- 2,4-dinitrobenzene （DFDNB） under mild conditions. In the process, four intermediates wer...A novel benzo [ 1,5] oxazepin-4-one skeleton compound and its four derivatives were synthesized effectively from 1,5-difluoro- 2,4-dinitrobenzene （DFDNB） under mild conditions. In the process, four intermediates were synthesized by substitutions of the two fluorine atoms and reductions of the meta-dinitro groups in DFDNB respectively. The results showed that the key for synthesizing the intermediates was the substitution of one of the two fluorine atoms in DFDNB by 3-hydroxy butyric acid ethyl ester first, then the other fluorine atom by morpholine, and then the reduction of the meta-dinitro groups in the substitute by HCOONH4 with Pd/C. The products were purified with silica gel column chromatography, and confirmed by HPLC, LC-MS and 1H NMR. They should contribute to construct the molecular libraries for therapeutic applications.展开更多
The title compound （C16H15N3O2, Mr= 281.31） has been synthesized and characterized by elemental analysis and single-crystal X-ray diffraction. The Schiff base compound is a derivative of 4-aminoantipyrine. As expect...The title compound （C16H15N3O2, Mr= 281.31） has been synthesized and characterized by elemental analysis and single-crystal X-ray diffraction. The Schiff base compound is a derivative of 4-aminoantipyrine. As expected, the molecular structure adopts a trans configuration about the C=N double bond. It crystallizes in the monoclinic system, space group P2 1/c with a = 11.150（3）, b = 9.906（3）, c = 13.624（4） A, β = 106.360（4）°, V= 1443.9（7） ,A^3, Z = 4, Dc = 1.294 g/cm^3, F（000） = 592,μ（MoKa） = 0.088 mm ^-1, R = 0.0577 and wR = 0.1214. Of the 5766 total reflections, 2540 were unique. In the molecule there exist two different planes of pyrazoline and O（2）-C（10） phenyl ring, which are approximately coplanar （r.m.s. de deviation from the combined mean plane is 0026 A） with the dihedral angle between them of 6.3°.展开更多
文摘Sulfanilic acid has been found to be an efficient catalyst for the synthesis of 1,5-benzodiazepines from o-phenylenediamine and ketones. This method is simple, effective and environmentally friendly and gives better yields.
基金financial support from the National Natural Science Foundation of China(No.21276064)the Natural Science Foundation of Hebei Education Department(No.2008320)the Science Foundation of Hebei Normal University(No.2011Y04)
文摘A general, mild and efficient protocol for the synthesis of ethyl 4-methyl-2-（thiophen）-2,5-dihydro-1,5- benzodiazepine-3-carboxylate is achieved for first time using H3PMo12O40 in ethanol at 0 ℃ by a one- pot, three-component condensation of various thiophene aldehydes, substituted o-phenylenediamines and ethyl acetoacetate. Compared with the conventional synthesis method, this procedure has the advantages of convenient operation, excellent yields, and environmentally benign. A plausible formation mechanism has been proposed. The structure of the products is characterized by1H NMR, IR, MS and elemental analysis.
文摘MgBr2 performs as a novel catalyst for the synthesis of various 1,5-benzodiazepine derivatives from wide range of substituted o- phenylenediamines and various ketones in good to excellent isolated yields （93-98%） using water as solvent at ambient temperature. Several solvents were examined for this reaction; however, in terms of reaction yield and time, water was found to be the optimum solvent. The remarkable advantages offered by this method are easily and inexpensive available catalyst, simple procedure, mild conditions, much faster （40-60 man） reactions and good to excellent yields of products.
文摘Borax/phosphorous oxychloride （BPO） efficiently catalyzes the preparation of 1,5-benzodiazepine derivatives of o-phenylenediamines and ketones in solvent-free and solution conditions. The reaction proceeds efficiently under ambient conditions giving excellent yields of the products. This new protocol allows the recycling of catalyst with no loss in its potency.
文摘Three kinds of products have been separated from the reaction mixtures of 1,2-dihydro-2, 4-disubstituted-1,5-benzodiazepine with: CCI_2.Besides the addition products of: CCI_2 to C=N.the inserted products of: CCI_2 to N-H and C-H single bonds were obtained, too.
文摘The title compound C18H16N4O3 （Mr = 336.35） has been synthesized and characterized by elemental analysis and single-crystal X-ray diffraction. The Schiff base compound is a derivative of 4-aminoantipyrine. As expected, the molecular structure adopts a trans configuration about the central C=N double bond. It crystallizes in orthorhombic, space group P2dc with a = 7.632（1）, b = 7.816（1）, c = 28.082（5） A,β = 96.18（1）°, V= 1665.48（51） A^3, Z= 4, Dc = 1.341 g/cm^3, F（000） = 704,μ = 0.094 mm^-1, the final R = 0.0448 and wR = 0.1058. Of the total 3748 collections, 3105 were unique. In the molecule there exist two different planes of pyrazoline and C（11）-C（16） phenyl ring, which are approximately coplanar （r.m.s. de deviation from the combined mean plane is 0.03 A） with the dihedral angle between them of 9.8%.
基金Institute of Materia Medica,Chinese Academy of Medical Sciences & Peking Union Medical College for ~1H NMR and Mass spectral determinations,and providing some financial support for this project.
文摘A novel benzo [ 1,5] oxazepin-4-one skeleton compound and its four derivatives were synthesized effectively from 1,5-difluoro- 2,4-dinitrobenzene （DFDNB） under mild conditions. In the process, four intermediates were synthesized by substitutions of the two fluorine atoms and reductions of the meta-dinitro groups in DFDNB respectively. The results showed that the key for synthesizing the intermediates was the substitution of one of the two fluorine atoms in DFDNB by 3-hydroxy butyric acid ethyl ester first, then the other fluorine atom by morpholine, and then the reduction of the meta-dinitro groups in the substitute by HCOONH4 with Pd/C. The products were purified with silica gel column chromatography, and confirmed by HPLC, LC-MS and 1H NMR. They should contribute to construct the molecular libraries for therapeutic applications.
基金This work was supported by the Phytochemistry Key Laboratory of Shaanxi Province (No. 02js40)
文摘The title compound （C16H15N3O2, Mr= 281.31） has been synthesized and characterized by elemental analysis and single-crystal X-ray diffraction. The Schiff base compound is a derivative of 4-aminoantipyrine. As expected, the molecular structure adopts a trans configuration about the C=N double bond. It crystallizes in the monoclinic system, space group P2 1/c with a = 11.150（3）, b = 9.906（3）, c = 13.624（4） A, β = 106.360（4）°, V= 1443.9（7） ,A^3, Z = 4, Dc = 1.294 g/cm^3, F（000） = 592,μ（MoKa） = 0.088 mm ^-1, R = 0.0577 and wR = 0.1214. Of the 5766 total reflections, 2540 were unique. In the molecule there exist two different planes of pyrazoline and O（2）-C（10） phenyl ring, which are approximately coplanar （r.m.s. de deviation from the combined mean plane is 0026 A） with the dihedral angle between them of 6.3°.
