An efficient,economical,and phosgene-free approach was developed for the preparation of l,4-dihydro-2H-3,l-benzoxazin-2-one from 2-aminobenzyl alcohol.In terms of its key features,this reaction uses the cheap and recy...An efficient,economical,and phosgene-free approach was developed for the preparation of l,4-dihydro-2H-3,l-benzoxazin-2-one from 2-aminobenzyl alcohol.In terms of its key features,this reaction uses the cheap and recyclable non-metal selenium as a catalyst instead of the noble metal palladium;carbon monoxide as a carbonylation agent instead of virulent phosgene or one of its derivatives;and oxygen as an oxidant.The selenium-catalyzed oxidative carbonylation reaction of2-aminobenzyl alcohol proceeded efficiently in a single pot in the presence of triethylamine to afford l,4-dihydro-2H-3,l-benzoxazin-2-one in 87%yield.Furthermore,the selenium catalyst was readily recovered and recycled,affording a product yield of 80%after five cycles.展开更多
The title compound, 4-tert-butyl-6-（4-chlorophenyl）-3,6-dihydro-2H-1,3-thiazin- 2-iminium chloride （C14H18C12N2S）, has been synthesized by the reaction of 1-（4-chlorophenyl）- 4,4-dimethylpent-1-en-3-one with thi...The title compound, 4-tert-butyl-6-（4-chlorophenyl）-3,6-dihydro-2H-1,3-thiazin- 2-iminium chloride （C14H18C12N2S）, has been synthesized by the reaction of 1-（4-chlorophenyl）- 4,4-dimethylpent-1-en-3-one with thiourea, and its crystal structure was determined by single- crystal X-ray diffraction. The crystal belongs to the monoclinic system, space group P211c with a = 16.3064（11）, b = 9.4471（6）, c = 11.2626 （8）A, β = 108.400（1）°, Z = 4, V = 1646.28（19） A^3, Mr = 317.26, Dc = 1.280 g/cm^3, S = 1.078,μ = 0.510 mm^-1, F（000） = 664, the final R = 0.0514 and wR = 0.1412 for 3210 observed reflections （I 〉 2σ（I））. The thiazine ring system displays a twisted boat conformation, and three N-H,..Cl hydrogen bonds exist in the crystal. The combination of two N-H...Cl hydrogen bonds generate an R2^1 （6） ring.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
The title compound tert-butyl 4-[（E）-4-（1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl）- 1-butenyl] benzoate has been synthesized and characterized by X-ray crystallography. It crystallizes in monoclinic, space group C2/c...The title compound tert-butyl 4-[（E）-4-（1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl）- 1-butenyl] benzoate has been synthesized and characterized by X-ray crystallography. It crystallizes in monoclinic, space group C2/c with a = 14.875（3）, b = 8.9796（13）, c = 34.736（6） A°, β = 95.981（4）°, V= 4614.4（14）A°^3, Z= 8, Dc = 1.213 g/cm^3, F（000） = 1792,μ（MoKα） = 0.084 mm^-1, R = 0.0602 and wR = 0.1445 for 4613 unique reflections with 2272 observed ones （I〉 2σ（I））. The results of crystal structure determination show that the title compound has a layer structure, and the two benzene rings in molecule are parallel to each other.展开更多
基金supported by the Program for Changjiang Scholars and Innovative Research Team in University(IRT1061)the Program for Innovative Research Team in Science and Technology in University of Henan Province(15IRTSTHN003)+1 种基金the Young Backbone Teachers Training Fund of the Education Department of Henan Province(2013GGJS-059)Henan Normal University(2011-8)
文摘An efficient,economical,and phosgene-free approach was developed for the preparation of l,4-dihydro-2H-3,l-benzoxazin-2-one from 2-aminobenzyl alcohol.In terms of its key features,this reaction uses the cheap and recyclable non-metal selenium as a catalyst instead of the noble metal palladium;carbon monoxide as a carbonylation agent instead of virulent phosgene or one of its derivatives;and oxygen as an oxidant.The selenium-catalyzed oxidative carbonylation reaction of2-aminobenzyl alcohol proceeded efficiently in a single pot in the presence of triethylamine to afford l,4-dihydro-2H-3,l-benzoxazin-2-one in 87%yield.Furthermore,the selenium catalyst was readily recovered and recycled,affording a product yield of 80%after five cycles.
基金supported by the National Project of Scientific and Technical Supporting Programs Funded by Ministry of Science & Technology of China (No 2006BAE01A01-4)
文摘The title compound, 4-tert-butyl-6-（4-chlorophenyl）-3,6-dihydro-2H-1,3-thiazin- 2-iminium chloride （C14H18C12N2S）, has been synthesized by the reaction of 1-（4-chlorophenyl）- 4,4-dimethylpent-1-en-3-one with thiourea, and its crystal structure was determined by single- crystal X-ray diffraction. The crystal belongs to the monoclinic system, space group P211c with a = 16.3064（11）, b = 9.4471（6）, c = 11.2626 （8）A, β = 108.400（1）°, Z = 4, V = 1646.28（19） A^3, Mr = 317.26, Dc = 1.280 g/cm^3, S = 1.078,μ = 0.510 mm^-1, F（000） = 664, the final R = 0.0514 and wR = 0.1412 for 3210 observed reflections （I 〉 2σ（I））. The thiazine ring system displays a twisted boat conformation, and three N-H,..Cl hydrogen bonds exist in the crystal. The combination of two N-H...Cl hydrogen bonds generate an R2^1 （6） ring.
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The title compound tert-butyl 4-[（E）-4-（1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl）- 1-butenyl] benzoate has been synthesized and characterized by X-ray crystallography. It crystallizes in monoclinic, space group C2/c with a = 14.875（3）, b = 8.9796（13）, c = 34.736（6） A°, β = 95.981（4）°, V= 4614.4（14）A°^3, Z= 8, Dc = 1.213 g/cm^3, F（000） = 1792,μ（MoKα） = 0.084 mm^-1, R = 0.0602 and wR = 0.1445 for 4613 unique reflections with 2272 observed ones （I〉 2σ（I））. The results of crystal structure determination show that the title compound has a layer structure, and the two benzene rings in molecule are parallel to each other.
