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发展了一条1,2,6,7-四氢-8H-茚并[5,4-b]呋喃-8-酮的新合成方法,以价廉、易得的对溴苯酚为原料,在无水碳酸钾作用下与2-溴乙醛缩二乙醇缩合后用多聚磷酸(PPA)环合得5-溴苯并呋喃,该中间体与丙烯酸甲酯在Pd(OAc)2催化下,经Heck偶合反应得3-(苯并呋喃-5-基)丙酸甲酯,在氢氧化钠水溶液中经Raney Ni催化氢化和水解一锅反应得3-(2,3-二氢苯并呋喃-5-基)丙酸,再经二溴代、Friedel-Crafts酰化反应和氢解脱溴,得1,2,6,7-四氢-8H-茚并[5,4-b]呋喃-8-酮,7步反应总收率49.9%.该方法原料易得、反应条件温和、操作简便、产物分离纯化容易,收率良好,适合大规模制备1,2,6,7-四氢-8H-茚并[5,4-b]呋喃-8-酮. 相似文献
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利用L-脯氨酸催化的5-氯水杨醛(1)与6-甲基-4-羟基吡喃酮(2)的缩合反应及硫酸铜催化下与1,3-二甲基-5-氨基吡唑(3)的串联反应,合成得到了10-氯-1,3-二甲基-5-(2-氧代丙基)色烯并[4,3-d]吡唑并[3,4-b]吡啶-6(3H)-酮(4)和10-氯-5-二乙氧基甲基-1,3-二甲基色烯并[4,3-d]吡唑并[3,4-b]吡啶-6(3H)-酮(5).化合物5的结构通过单晶X射线衍射法确定:晶体属于三斜晶系,空间群P-1;相对分子质量Mr=803.68;晶胞参数a=1.03160(10)nm,b=1.42900(13)nm,c=1.44268(15)nm;V=1.9448(3)nm~3;Z=2;晶胞密度Dc=1.372g/cm~3;吸收系数μ=0.228mm-1;单胞中电子的数目F(000)=840.晶体结构用直接法解出,经全矩阵最小二乘法对原子参数进行修正,最终的偏离因子为R=0.0681,w R=0.2051.在晶体结构中色烯环与吡啶环及吡唑环近似于共平面. 相似文献
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采用密度泛函理论(DFT) CAM-B3LYP方法对6,12-二乙炔基茚并[1,2-b]芴系列衍生物的极化率(αs)和第二超极化率(γs)进行研究. 结果表明, 此类分子具有较大的γs值. 用乙炔基硅烷基和氧原子取代茚并[1,2-b]芴分子6,12位的氢原子后, 分子的几何构型发生改变, 进而影响其非线性光学(NLO)性质. 连接乙炔基硅烷基的分子αs值和γs值均增大, 而连接氧原子的分子αs值和γs值均减小. 茚并[1,2-b]芴环2,8位取代基R(R=H, F, CH3)的不同, 对分子的γs值也有一定的影响, R为CH3时分子的αs值和γs值均较大. 由含时密度泛函理论(TD-DFT)方法计算的吸收光谱分析可知, 与茚并[1,2-b]芴系列分子相比, 引入乙炔基硅烷基的分子共轭性增强, 最大吸收波长红移; 引入氧原子的分子几何结构扭曲, 共轭性降低, 最大吸收波长蓝移. 相似文献
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报道了以2-甲(乙)基苯胺1a,1b为原料经Sandmeyer反应得到7-甲(乙)基靛红2a,2b;再以环境友好的聚乙二醇-400为溶剂,N-溴代丁二酰亚胺(NBS)为绿色溴代试剂对2a,2b进行5位溴代,得到5-溴-7-甲(乙)基靛红3a,3b;2a,2b,3a,3b进一步氮烃基化得到1-烃基-7-甲(乙)基靛红4a~4j和1-烃基-5-溴-7-甲(乙)基靛红5a~5j.2a,2b,3a,3b,4a~4j,5a~5j分别与硫代氨基脲,在以二氧六环为溶剂,碳酸钾存在的条件下回流反应,简便地合成了24种5H-[1,2,4]三嗪并[5,6-b]吲哚-3-硫醇类杂环化合物6a~6x.大部分化合物未见文献报道,其结构经红外光谱、质谱、核磁氢谱(碳谱)和元素分析确认. 相似文献
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《化学研究与应用》2015,(7)
以吲哚3-羧酸甲酯为起始原料,经偶联、环化和卤代合成中间体(3)。对化合物3进行11位氨基修饰,制备了中间体(4和6)。在1H-吡唑-1-甲脒盐酸盐的作用下,合成具有潜在抗肿瘤活性的目标产物11-位胍基修饰的5-甲基-吲哚[2,3-b]喹啉衍生物(5a,5b和7)。目标产物5a,5b和7经红外光谱、核磁氢谱、碳谱、高分辨质谱等方法对其结构进行了确认,并进行了抗肿瘤活性初筛。结果显示,该方法可以方便有效地制备含胍基的5-甲基吲哚[2,3-b]喹啉衍生物。目标产物皆具有抗癌细胞增生的作用,其中5a活性最强,对A549细胞的IC50值达到0.78±0.09μM,且对三种癌细胞株都具有最好的抑制活性。 相似文献
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N. S. Prostakov Keti Sudzhi N. M. Mikhailova L. A. Murugova V. F. Zakharov 《Chemistry of Heterocyclic Compounds》1981,17(10):1038-1042
1-Methyl-1H-indeno[1,2-b]pyridine and 1-methyl-1H-5-(, -dicarbomethoxyvinyl)-(formyl, acetyl)indeno[3,2-b]pyridines were obtained by treatment of N-methyl-4-azafluorenium iodide, as well as mixtures of it with acetylenedicarboxylic ester, dimethylformamide (DMF), and phosphorus oxychloride or acetic anhydride, with bases. 4-Azafluoronenone was used to synthesize 9-(p-methoxyphenyl)-4-azafluoren-9-ol, which was reduced to 9-(p-methoxyphenyl)-4-azafluorene, and 1-methyl-1H-5-(p-methoxyphenyl)indeno[3,2-b]pyridine was obtained from the methiodide of the latter.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1382–1386, October, 1981. 相似文献
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Condensation of 1,2-indanedione and 1,2,3-indanetrione hydrate (ninhydrin) with 2,3-diamino-pyridines gave a number of compounds belonging to the hitherto unknown 6H-indeno[1,2-b]-pyrido[3,2-e]pyrazine ring system. The unsymmetrical nature of the reactants can theoretically result in isomeric ring closure products. Assignment of the 6H- ring system was based upon the identity of 6H-indeno[1,2-b]pyrido[3,2-e]pyrazin-6-one obtained from 2,3-diaminopyridine and ninhydrin with material prepared by unequivocal synthesis. The direction of cyclization of ninhydrin and 1,2-indanedione with the diamines was shown to be the same by reduction of the indenopyridopyrazinones to the corresponding indenopyridopyrazines. Some physical, chemical, and tumor growth-inhibitory properties of the products are reported. 相似文献
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An operationally simple, catalyst-free, and efficient protocol for the synthesis of novel 4H-indeno[1,2-b]furan-4-one and furo[2,3-d]pyrimidine derivatives by a one-pot reaction of 2-aminopyridines, 1,3-indandione, or barbituric acid and phenylglyoxal monohydrate in water at reflux, involving domino aldol condensation, Michael addition, and ring-closing reactions is described. This transformation has several advantages, including high yield, short reaction duration, simple workup, and simple purification. 相似文献
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N. S. Prostakov A. T. Soldatenkov V. O. Fedorov S. Mobio M. A. Galiullin 《Chemistry of Heterocyclic Compounds》1980,16(11):1149-1153
It was established that N-phenacyl and p-nitrophenacyl bromides and N-methyl-1-azafluorenium iodide, as well as N-phenacyl-7-nitro-1-azafluorenium bromide, are converted to N-substituted 1H-indeno[2,1-b]pyridines rather than to the corresponding yilds or indenoindolizines upon treatment with bases under various conditions. All of the pseudoazulenes of this type were isolated in the form of crystalline black or dark-violet substances. In contrast to pseudoazulenes of the 1H-indeno[1,2-b]-and 2H-indeno[2,1-c]pyridine series, they are stable both in the solid state and in solutions. 1H-1-Methylindeno[2,1-b]pyridine forms a perchlorate and a picrate (retention of the pseudoazulene structure) but is converted to N-methyl-1-azafluorenium chloride by the action of hydrogen chloride. Spectral characteristics are presented for all of the compounds obtained.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1511–1515, November, 1980. 相似文献
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Benzo[4,5]cyclohepta[1,2-b]quinoxaIine 2 , benzo[4,5]cyclohepta[1,2-b]pyrazine 3a and benzo[4,5]cyclohepta[1,2-b]quinoxaline 4 were prepared from 4,5-benzotropolone and 1,2-phenylenediamine, ethylenediamine and 1,2-diaminocyclohexane, respectively. Compound 3a was methylated to 3b . 相似文献
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Tye synthesis of thieno[3,2-c]cinnoline is described; vapour phase thermolysis of this compound gives benzo[3,4]cyclobuta[1,2-b]thiophene. 相似文献
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A. Monge J. A. Palop T. Goñi A. Martinez E. Fernández-Alvarez 《Journal of heterocyclic chemistry》1984,21(2):381-384
The synthesis of two new derivatives of 3H[1,2]diazepino[5,6-b]indole, 5 and 11 , and one new derivative of 3H[1,2]diazepino[4,5-b]indole, 16 , are described. Compound 5 was obtained by the reaction of methyl 2-(3-methoxycarbonyl-1-methylindole)acetate 2 , with hydrazine. Compound 11 was obtained in two ways from ethyl 2-(1-methylindole)acetate ( 8 ) by formylation and reaction with hydrazine. Compound 16 was obtained treating 3-(2-ethoxycarbonylindole)acetonitrile ( 14 ) with hydrazine. 相似文献