The title compound （ethyl5-（4-（2-phenylacetamido）phenyl）-lH-pyrazole-3-carboxylate, C20H19N3O3） was synthesized by the reaction of Claisen condensation, cyclization, reduction and acylation. The structure was ch...The title compound （ethyl5-（4-（2-phenylacetamido）phenyl）-lH-pyrazole-3-carboxylate, C20H19N3O3） was synthesized by the reaction of Claisen condensation, cyclization, reduction and acylation. The structure was characterized by X-ray diffraction, MS, NMR and IR. It belongs to the monoclinic system, space group C2/c with a = 22.723（9）, b = 9.324（4）, c = 18.890（8） A, β = 114.259（6）°, V = 3649（3） A^3, Dc = 1.272 Mg·m^3, Z = 8, Mr = 349.38, p = 0.087 mm^-1, F（000） = 1472, the final R = 0.0615 and wR = 0.1643. The biological test shows that the title compound has a moderate acrosin inhibition activity.展开更多
The crystal structure of the title compound（C19H15F3N2O2,Mr = 360.33） was determined by single-crystal X-ray diffraction.The crystal belongs to triclinic,space group P1,with a = 6.5604（7）,b = 13.9614（16）,c = 18....The crystal structure of the title compound（C19H15F3N2O2,Mr = 360.33） was determined by single-crystal X-ray diffraction.The crystal belongs to triclinic,space group P1,with a = 6.5604（7）,b = 13.9614（16）,c = 18.1790（18） ,α = 102.749（7）,β = 97.542（6）,γ = 94.355（4）°,V = 1600.5（3） 3,Z = 4,Dc = 1.495 g/cm3,λ（MoKα） = 0.71070,F（000） = 744,μ（MoKα） = 0.122 mm-1,R = 0.0434 and wR = 0.1051.A total of 7590 unique reflections were collected,of which 5429 with ｜F｜2 ≥ 2σ｜F｜2 were observed.The two cyclohexene rings in the molecule adopt boat-boat conformations with the deviations of ring atoms C（9） and C10 from the C（5）/C（6）/C（7）/C（8） plane（Ⅰ） by 1.1204（0.0023） and 1.1132（0.0023） ,respectively,whereas from the C（2）/C（3）/C（5）/C（8） plane（Ⅱ） by 1.1627（0.0022） and 1.1818（0.0021） ,respectively.In the cyclopropane and lactam rings,atoms C（11） and N（1） point towards the double bond of C（9）-C（10） and the dihedral angle between the ring plane（Ⅲ） containing C（1）,C（2）,C（3） and C（4） and plane（IV） consisting of C（6）,C（7） and C（11） is 55.76（0.07）°.The dihedral angles between planes Ⅳ and Ⅰ and Ⅱ and Ⅲare 63.58（0.07）° and 58.10（0.06）°,respectively.The dihedral angle between the benzene ring C（13）～ C（18） and plane Ⅳ is 42.41（0.06）°.展开更多
A series of novel 5-（trifluoromethyl）-1H-pyrazole-4-carboxamide derivatives（6a–6n, 7a, 7b, and 8a-8f）were synthesised by placing the amide bond at the 4-position of the pyrazole ring. These derivatives differed f...A series of novel 5-（trifluoromethyl）-1H-pyrazole-4-carboxamide derivatives（6a–6n, 7a, 7b, and 8a-8f）were synthesised by placing the amide bond at the 4-position of the pyrazole ring. These derivatives differed from the structure of chlorantraniliprole analogues with the amide bond at the 5-position of the pyrazole ring. Preliminary bioassay results revealed that a few title compounds exhibited good insecticidal activities against lepidopteran pests, such as Plutella xylostella, Mythimna separate, Heliothis armigera, and Ostrinia nubilalis. Some title compounds also elicited broad-spectrum insecticidal activities against dipterous insects including Culex pipiens pallens after altering the amide position. Similar to pyrazole-5-carboxamide analogues, compounds 6b and 6e showed 100% insecticidal activity against P. xylostella, C. pipiens pallens, and M. separate at concentrations of 200, 2, and 200 mg/m L, respectively.This finding suggested that 5-（trifluoromethyl）-1H-pyrazole-4-carboxamide derivatives are potential alternative insecticides for management of agriculture pests.展开更多
Refluxing of (E)-5-amino-1-phenyl-3-styryl-1H-pyrazole-4-carbonitrile 2 with triethylor-thoformate in acetic anhydride afforded the corresponding formimidate 3. Treatment of 3 with hydrazine hydrate in ethanol afforde...Refluxing of (E)-5-amino-1-phenyl-3-styryl-1H-pyrazole-4-carbonitrile 2 with triethylor-thoformate in acetic anhydride afforded the corresponding formimidate 3. Treatment of 3 with hydrazine hydrate in ethanol afforded amino imino compound 4. Reaction of 4 with diethyl dicarbonate at reflux gave (E)-7-phenyl-9-styryl-7H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidine 7. Refluxing of 4 with hydrazine hydrate afforded (E)-4-hydrazinyl-1-phenyl-3-styryl-1H-pyrazolo[3,4-d] pyrimidine 8. Treatment of the latter compound 8 with aldehydes in boiling ethanol in the presence of acetic acid afforded the corresponding hydrazone 10. Oxidative cyclization of the hydrazone 10 led to the formation of pyrazolo[4,3-e][1,2,4]triazolo[4,3-c]pyrimidine 11. The latter products re-arranged to pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidines 13. The structures of the new products were established on the basis of elemental analysis and spectral data.展开更多
基金supported by the Science and technology support program of Jiangsu Province (2010, BE2010682)
文摘The title compound （ethyl5-（4-（2-phenylacetamido）phenyl）-lH-pyrazole-3-carboxylate, C20H19N3O3） was synthesized by the reaction of Claisen condensation, cyclization, reduction and acylation. The structure was characterized by X-ray diffraction, MS, NMR and IR. It belongs to the monoclinic system, space group C2/c with a = 22.723（9）, b = 9.324（4）, c = 18.890（8） A, β = 114.259（6）°, V = 3649（3） A^3, Dc = 1.272 Mg·m^3, Z = 8, Mr = 349.38, p = 0.087 mm^-1, F（000） = 1472, the final R = 0.0615 and wR = 0.1643. The biological test shows that the title compound has a moderate acrosin inhibition activity.
文摘The crystal structure of the title compound（C19H15F3N2O2,Mr = 360.33） was determined by single-crystal X-ray diffraction.The crystal belongs to triclinic,space group P1,with a = 6.5604（7）,b = 13.9614（16）,c = 18.1790（18） ,α = 102.749（7）,β = 97.542（6）,γ = 94.355（4）°,V = 1600.5（3） 3,Z = 4,Dc = 1.495 g/cm3,λ（MoKα） = 0.71070,F（000） = 744,μ（MoKα） = 0.122 mm-1,R = 0.0434 and wR = 0.1051.A total of 7590 unique reflections were collected,of which 5429 with ｜F｜2 ≥ 2σ｜F｜2 were observed.The two cyclohexene rings in the molecule adopt boat-boat conformations with the deviations of ring atoms C（9） and C10 from the C（5）/C（6）/C（7）/C（8） plane（Ⅰ） by 1.1204（0.0023） and 1.1132（0.0023） ,respectively,whereas from the C（2）/C（3）/C（5）/C（8） plane（Ⅱ） by 1.1627（0.0022） and 1.1818（0.0021） ,respectively.In the cyclopropane and lactam rings,atoms C（11） and N（1） point towards the double bond of C（9）-C（10） and the dihedral angle between the ring plane（Ⅲ） containing C（1）,C（2）,C（3） and C（4） and plane（IV） consisting of C（6）,C（7） and C（11） is 55.76（0.07）°.The dihedral angles between planes Ⅳ and Ⅰ and Ⅱ and Ⅲare 63.58（0.07）° and 58.10（0.06）°,respectively.The dihedral angle between the benzene ring C（13）～ C（18） and plane Ⅳ is 42.41（0.06）°.
基金financially supported by the Key Technologies R&D Program (No. 2014BAD23B01)National Natural Science Foundation of China (Nos. 21202025, 21372052)
文摘A series of novel 5-（trifluoromethyl）-1H-pyrazole-4-carboxamide derivatives（6a–6n, 7a, 7b, and 8a-8f）were synthesised by placing the amide bond at the 4-position of the pyrazole ring. These derivatives differed from the structure of chlorantraniliprole analogues with the amide bond at the 5-position of the pyrazole ring. Preliminary bioassay results revealed that a few title compounds exhibited good insecticidal activities against lepidopteran pests, such as Plutella xylostella, Mythimna separate, Heliothis armigera, and Ostrinia nubilalis. Some title compounds also elicited broad-spectrum insecticidal activities against dipterous insects including Culex pipiens pallens after altering the amide position. Similar to pyrazole-5-carboxamide analogues, compounds 6b and 6e showed 100% insecticidal activity against P. xylostella, C. pipiens pallens, and M. separate at concentrations of 200, 2, and 200 mg/m L, respectively.This finding suggested that 5-（trifluoromethyl）-1H-pyrazole-4-carboxamide derivatives are potential alternative insecticides for management of agriculture pests.
文摘Refluxing of (E)-5-amino-1-phenyl-3-styryl-1H-pyrazole-4-carbonitrile 2 with triethylor-thoformate in acetic anhydride afforded the corresponding formimidate 3. Treatment of 3 with hydrazine hydrate in ethanol afforded amino imino compound 4. Reaction of 4 with diethyl dicarbonate at reflux gave (E)-7-phenyl-9-styryl-7H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidine 7. Refluxing of 4 with hydrazine hydrate afforded (E)-4-hydrazinyl-1-phenyl-3-styryl-1H-pyrazolo[3,4-d] pyrimidine 8. Treatment of the latter compound 8 with aldehydes in boiling ethanol in the presence of acetic acid afforded the corresponding hydrazone 10. Oxidative cyclization of the hydrazone 10 led to the formation of pyrazolo[4,3-e][1,2,4]triazolo[4,3-c]pyrimidine 11. The latter products re-arranged to pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidines 13. The structures of the new products were established on the basis of elemental analysis and spectral data.
