氨基磺酸催化的二吲哚基甲烷衍生物的研磨法合成
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摘要
通过简单的机械研磨,在x(氨基磺酸)=10%催化作用下,室温将吲哚与一系列醛类物质转化为二吲哚基甲烷类衍生物.共合成得到15个化合物,其结构经1 H NMR,13 C NMR及元素分析确定.同时,对催化剂的最佳用量和重复使用性能进行了探究.结果表明,催化剂的最佳用量为x(氨基磺酸)=10%,并在重复使用6次后依然保持较高的催化活性.
By means of mechanical grinding under catalysis of x(sulfamic acid)=10%at indoor temperature,the indole and a series of aldehydes were transformed into a class of bis(indol-3-yl)methanes,amounting to 15 chemical compounds and their structure was determined with 1 H NMR,13 C NMR,and elemental analysis.Meantime,the optimal amount of catalyst and its performance of recycled utilization were probed.The result showed that the optimal amount of the catalyst would be x(sulfamic acid)=10%and the catalytic activity of the catalyst would still remain higher after 6 times of recycle.
By means of mechanical grinding under catalysis of x(sulfamic acid)=10%at indoor temperature,the indole and a series of aldehydes were transformed into a class of bis(indol-3-yl)methanes,amounting to 15 chemical compounds and their structure was determined with 1 H NMR,13 C NMR,and elemental analysis.Meantime,the optimal amount of catalyst and its performance of recycled utilization were probed.The result showed that the optimal amount of the catalyst would be x(sulfamic acid)=10%and the catalytic activity of the catalyst would still remain higher after 6 times of recycle.
引文
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[22]PATIL D V,DERE B G,REGE A P,et al.Synthesis of bis(indolyl)methanes in catalyst-free and solvent-free conditions[J].Synthetic Communications,2011,41(5):736-747.
[23]LI J T,SUN S F.Synthesis of diindolylmethanes(DIMs)catalyzed by silicotungstic acid by grinding method[J].Journal of Chemistry,2010,7(3):922-926.
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[2]朱伟,刘华章,杨光宇,等.二吲哚甲烷诱导荷鼻咽癌裸鼠肿瘤转归及对MDA、SOD和GSH-Px的影响[J].中山大学学报:医学科学版,2009,30(增刊):60-63.
[3]刘艳波,赵丽娟,郭亚雄,等.DIM联合顺铂诱导PC-3细胞凋亡机制的研究[J].中国实验诊断学,2008,12(11):1416-1419.
[4]SHIRI M,ZOLFIGOL M A,KRUGER H G,et al.Bis-and Trisindolylmethanes(BIMs and TIMs)[J].Chemical reviews,2009,110(4):2250-2293.
[5]LOUNASMAA M,TOLVANEN A.Simple indole alkaloids and those with a nonrearranged monoterpenoid unit[J].Natural product reports,2000,17(2):175-191.
[6]KAMAL A,QURESHI A A.Syntheses of some substituted diindolylmethanes in aqueous medium at room temperature[J].Tetrahedron,1963,19(4):513-520.
[7]GREGOROVICKH B V,LIANGO S Y,CLUGSTON D M,et al.Reductive C-alkylationl[J].Candadian Journal of Chemistry,1968,46(21):3291-3300.
[8]NAGAWADE R R,SHINDE D B.Zirconyl(IV)chloride-catalysed reaction of indoles:an expeditious synthesis of bis(indolyl)methanes[J].Acta chimica slovenica,2006,53:210-213.
[9]ZHANG Z H,YIN L,WANG Y M.An efficient and practical process for the synthesis of bis(indolyl)methanes catalyzed by zirconium tetrachloride[J].Synthesis,2005,12:1949-1954.
[10]SHIRINI F,KHALIGH N G,JOLODAR O G.An efficient and practical synthesis of bis(indolyl)methanes catalyzed by N-sulfonic acid poly(4-vinylpyridinium)chloride[J].Dyes and Pigments,2013,98:290-296.
[11]TAYEBEE R,AMINI M M,NEHZAT F,et al.H5PW10V2O40pyridino-SBA-15as a highly recyclable,robust and efficient inorganic-organic hybrid material for the catalytic preparation[J].Journal of Molecular Catalysis A:Chemical,2013,366:140-148.
[12]VEISI1 H,HEMMATI S,VEISI H.Highly Efficient Method for Synthesis of Bis(indolyl)methanes Catalyzed by FeCl3-based Ionic Liquid[J].Journal of the Chinese Chemical Society,2009,56(2):240-245.
[13]MENDES S R,THUROW S,FORTES M P,et al.Synthesis of bis(indolyl)methanes using silica gel as an efficient and recyclable surface[J].Tetrahedron Letters,2012,53(40):5402-5406.
[14]OLYAEIA,VAZIRI M,RAZEGHI R,et al.A novel approach to bis(indolyl)methanes using nickel nanoparticles as a reusable catalyst under solvent-free conditions[J].Journal of the Serbian Chemical Society,2013,78(4):463-468.
[15]DHUMASKAR K L,TILVE S G.Synthesis of bis(indolyl)methanes under catalyst-free and solvent-free conditions[J].Green Chemistry Letters and Reviews,2012,5(3):353-402.
[16]LI J T,DAI H G,XU W Z,et al.An efficient and practical synthesis of bis(indolyl)methanes catalyzed by aminosulfonic acid under ultrasound[J].Ultrasonics sonochemistry,2006,13(1):24-27.
[17]LI W J,LIN X F,WANG J,et al.A mild and efficient synthesis of bis-indolylmethanes catalyzed by sulfamic acid[J].Analytical Letters,2005,35(21):2765-2769.
[18]楼海文,张婷,李凯,等.机械研磨法合成5-(2-硝基烷基)米氏酸衍生物[J].有机化学,2011,31(8):1258-1261.
[19]YANG Q,YIN Z L,OUYANG B L,et al.Pyridinium tribromide catalyzed condensation of indoles and aldehydes to form bisindolylalkanes[J].Chinese Chemical Letters,2011,22(5):515-518.
[20]OLYAEI A,VAZIRI M,RAZEGHI R,et al.A novel approach to bis(indolyl)methanes using nickel nanoparticles as a reusable catalyst under solvent-free conditions[J].Journal of the Serbian Chemical Society,2013,78(4):463-468.
[21]ZHANG Z H,YIN L,WANG Y M.An efficient and practical process for the synthesis of bis(indolyl)methanes catalyzed by zirconium tetrachloride[J].Synthesis,2005,12:1949-1954.
[22]PATIL D V,DERE B G,REGE A P,et al.Synthesis of bis(indolyl)methanes in catalyst-free and solvent-free conditions[J].Synthetic Communications,2011,41(5):736-747.
[23]LI J T,SUN S F.Synthesis of diindolylmethanes(DIMs)catalyzed by silicotungstic acid by grinding method[J].Journal of Chemistry,2010,7(3):922-926.
[24]HERAVI M M,BAGHERNEJAD B,OSKOOIE H A.Application of sulfamic acid in organic synthesis-A short review[J].Current Organic Chemistry,2009,13(10):1002-1014.
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