4-单取代-1H-1,2,3-三氮唑的合成研究
|
摘要
以甲氧基聚乙二醇(mPEG)为起始原料通过磺酰化、叠氮化反应合成叠氮基甲氧基聚乙二醇(mPEG-N_3,2);在铜催化下和芳香炔、脂肪炔发生1,3-偶极环加成反应合成甲氧基聚乙二醇-1,2,3-三氮唑(mPEG-1,2,3-triazoles,3);再于酸性条件下脱除甲氧基聚乙二醇(mPEG)制备4-单取代-1H-1,2,3-三氮唑(4),其结构经过MS及~1H NMR、~(13)C NMR确证。
mPEG-N_(3 )(2)was achieved by an efficient two step process from readily available mPEG.1,3-Dipolar cycloadditions of mPEG-N_(3 )(2)with a variety of alkyl or aryl alkynes by copper-catalyzed yield mPEG-1,2,3-triazoles(3)in nearly quantitative yields.The removal of the mPEG moiety from the 1,2,3-triazole nucleus was achieved by acidic cleavage of the cycloadducts(3)giving 4-monosubstituted-1H-1,2,3-Triazoles(4),which was characterized by mass spectrometry,~( 1)H NMR and ~(13)C NMR spectrometry.
mPEG-N_(3 )(2)was achieved by an efficient two step process from readily available mPEG.1,3-Dipolar cycloadditions of mPEG-N_(3 )(2)with a variety of alkyl or aryl alkynes by copper-catalyzed yield mPEG-1,2,3-triazoles(3)in nearly quantitative yields.The removal of the mPEG moiety from the 1,2,3-triazole nucleus was achieved by acidic cleavage of the cycloadducts(3)giving 4-monosubstituted-1H-1,2,3-Triazoles(4),which was characterized by mass spectrometry,~( 1)H NMR and ~(13)C NMR spectrometry.
引文
[1]Rostovtsev V,Fokin V,Sharpless K,et al.A stepwise huisgen cycloaddition process:copper(I)-catalyzed regio-selective ligation of azides and terminal alkynes[J].Angew Chem Int Ed,2002,41(14):2 596-2 599.
[2]Liu X,Su C H.Cu(I)-promoted one-pot synthesis of 1,4-disubstituted 1,2,3-triazoles from anti-3-aryl-2,3-dibromopropanoic acids and nitrobenzaldehydes[J].Synthetic Commun,2017,47(4):279-284.
[3]Huang Q,Zheng M,Yang S,et al.Structure-activity relationship and enzyme kinetic studies on 4-aryl-1H-1,2,3-triazoles as indoleamine 2,3-dioxygenase(IDO)inhibitors[J].Eur J Med Chem,2011,46(11):5 680-5 687.
[4]贾淑红,李翠平,何兴,等.哌啶链接1,2,3-三氮唑化合物的合成及抗细菌活性[J].化学研究与应用,2016,28(2):158-163.
[5]Mallemula V R,Sanghai N N,V.Himabindu V,Chakravarthy A K.Synthesis and characterization of antibacterial 2-(pyridin-3-yl)-1H-benzo[d]imidazoles and 2-(pyridin-3-yl)-3H-imidazo[4,5-b]pyridine derivatives[J].Res Chem Intermed,2015,41(4):2 125-2 138.
[6]Ferreira M L G,Pinheiro L C S,Santos-Filho O A,et al.Design,synthesis,and antiviral activity of new 1H-1,2,3-triazole nucleoside ribavirin analogs[J].Med Chem Res,2014,23(3):1 501-1 511.
[7]Yu X,Huang Z D,Liu W,et al.Palladium-catalyzed oxidative C-H/C-H cross-coupling of 1-substituted 1,2,3-triazoles with furans and thiophenes[J].Org Biomol Chem,2015,13(15):4 459-4 465.
[8]Shi S P,Kuang C X.Palladium-catalyzed ortho-alkoxylation of 2-aryl-1,2,3-triazoles[J].J Org Chem,2014,79(13):6 105-6 112.
[9]江玉波,赵芬,韩春美,等.4-单取代-1,2,3-三氮唑的合成进展(II)-通过去取代基反应[J].化学研究与应用,2014,26(12):1 831-1 838.
[10]Taherpour A A,Kheradmand K.One-pot microwave-assisted solvent free synthesis of simple alkyl 1,2,3-triazole-4-carboxylates by using trimethylsilyl azide[J].J Heterocyclic Chem,2009,46(1):131-133.
[11]Jind T,Shin Kamijo S,Yamamoto Y.Copper-catalyzed synthesis of N-unsubstituted 1,2,3-triazoles from nonactivated terminal alkynes[J].Eur J Org Chem,2004,18:3 789-3 791.
[12]Coelho A,Diz P,Caamano O.Polymer-supported 1,5,7-triazabicyclo[4.4.0]dec-5-ene as polyvalent ligands in the copper-catalyzed Huisgen 1,3-dipolar cycloaddition[J].Adv Synth Catal,2010,352(7):1 179-1 192.
[13]Barluenga J,Valdes V,Beltran G,et al.Developments in Pd catalysis:synthesis of 1H-1,2,3-triazoles from sodium azide and alkenyl bromides[J].Angew Chem In Ed,2006,45(41):6 893-6 896.
[14]Kalisiak J,Sharpless B K,Fokin V V.Efficient synthesis of 2-substituted-1,2,3-triazoles[J].Org Lett,2008,10(15):3 171-3 174.
[15]张文生,匡春香,杨青.NH-1,2,3-三唑合成进展[J].有机化学,2011,31(1):54-62.
[16]Garanti L,Molteni G.MeOPEG-bounded azide cycloadditions to alkynyl dipolarophiles[J].Tetrahedron Lett,2003,44(6):1 133-1 135.
[17]苏长会,刘霞,丁志远,等.甲氧基聚乙二醇-1,2-二硬脂酰甘油磷酰乙醇胺的合成[J].化学通报,2017,80(3):304-306.
[18]Zhang W,Kuang C,Yang Q.Palladium-catalyzed one-pot synthesis of 4-aryl-1H-1,2,3-triazoles from anti-3-aryl-2,3-dibromopropanoic acids and sodium azide[J].Synthesis,2010,42(2):283-287.
[19]Jiang Y,Kuang C,Yang Q.CuI-catalyzed synthesis of 4-aryl-1H-1,2,3-triazoles from anti-3-aryl-2,3-dibromopropanoic acids and sodium azide[J].Synthesis,2010,42(24):4 256-4 260.
[20]Farooq T,Sydnes L K,Tornroos K W,et al.Debenzylation of functionalized 4-and 5-substituted 1,2,3-triazoles[J].Synthesis,2012,44(13):2 070-2 078.
[2]Liu X,Su C H.Cu(I)-promoted one-pot synthesis of 1,4-disubstituted 1,2,3-triazoles from anti-3-aryl-2,3-dibromopropanoic acids and nitrobenzaldehydes[J].Synthetic Commun,2017,47(4):279-284.
[3]Huang Q,Zheng M,Yang S,et al.Structure-activity relationship and enzyme kinetic studies on 4-aryl-1H-1,2,3-triazoles as indoleamine 2,3-dioxygenase(IDO)inhibitors[J].Eur J Med Chem,2011,46(11):5 680-5 687.
[4]贾淑红,李翠平,何兴,等.哌啶链接1,2,3-三氮唑化合物的合成及抗细菌活性[J].化学研究与应用,2016,28(2):158-163.
[5]Mallemula V R,Sanghai N N,V.Himabindu V,Chakravarthy A K.Synthesis and characterization of antibacterial 2-(pyridin-3-yl)-1H-benzo[d]imidazoles and 2-(pyridin-3-yl)-3H-imidazo[4,5-b]pyridine derivatives[J].Res Chem Intermed,2015,41(4):2 125-2 138.
[6]Ferreira M L G,Pinheiro L C S,Santos-Filho O A,et al.Design,synthesis,and antiviral activity of new 1H-1,2,3-triazole nucleoside ribavirin analogs[J].Med Chem Res,2014,23(3):1 501-1 511.
[7]Yu X,Huang Z D,Liu W,et al.Palladium-catalyzed oxidative C-H/C-H cross-coupling of 1-substituted 1,2,3-triazoles with furans and thiophenes[J].Org Biomol Chem,2015,13(15):4 459-4 465.
[8]Shi S P,Kuang C X.Palladium-catalyzed ortho-alkoxylation of 2-aryl-1,2,3-triazoles[J].J Org Chem,2014,79(13):6 105-6 112.
[9]江玉波,赵芬,韩春美,等.4-单取代-1,2,3-三氮唑的合成进展(II)-通过去取代基反应[J].化学研究与应用,2014,26(12):1 831-1 838.
[10]Taherpour A A,Kheradmand K.One-pot microwave-assisted solvent free synthesis of simple alkyl 1,2,3-triazole-4-carboxylates by using trimethylsilyl azide[J].J Heterocyclic Chem,2009,46(1):131-133.
[11]Jind T,Shin Kamijo S,Yamamoto Y.Copper-catalyzed synthesis of N-unsubstituted 1,2,3-triazoles from nonactivated terminal alkynes[J].Eur J Org Chem,2004,18:3 789-3 791.
[12]Coelho A,Diz P,Caamano O.Polymer-supported 1,5,7-triazabicyclo[4.4.0]dec-5-ene as polyvalent ligands in the copper-catalyzed Huisgen 1,3-dipolar cycloaddition[J].Adv Synth Catal,2010,352(7):1 179-1 192.
[13]Barluenga J,Valdes V,Beltran G,et al.Developments in Pd catalysis:synthesis of 1H-1,2,3-triazoles from sodium azide and alkenyl bromides[J].Angew Chem In Ed,2006,45(41):6 893-6 896.
[14]Kalisiak J,Sharpless B K,Fokin V V.Efficient synthesis of 2-substituted-1,2,3-triazoles[J].Org Lett,2008,10(15):3 171-3 174.
[15]张文生,匡春香,杨青.NH-1,2,3-三唑合成进展[J].有机化学,2011,31(1):54-62.
[16]Garanti L,Molteni G.MeOPEG-bounded azide cycloadditions to alkynyl dipolarophiles[J].Tetrahedron Lett,2003,44(6):1 133-1 135.
[17]苏长会,刘霞,丁志远,等.甲氧基聚乙二醇-1,2-二硬脂酰甘油磷酰乙醇胺的合成[J].化学通报,2017,80(3):304-306.
[18]Zhang W,Kuang C,Yang Q.Palladium-catalyzed one-pot synthesis of 4-aryl-1H-1,2,3-triazoles from anti-3-aryl-2,3-dibromopropanoic acids and sodium azide[J].Synthesis,2010,42(2):283-287.
[19]Jiang Y,Kuang C,Yang Q.CuI-catalyzed synthesis of 4-aryl-1H-1,2,3-triazoles from anti-3-aryl-2,3-dibromopropanoic acids and sodium azide[J].Synthesis,2010,42(24):4 256-4 260.
[20]Farooq T,Sydnes L K,Tornroos K W,et al.Debenzylation of functionalized 4-and 5-substituted 1,2,3-triazoles[J].Synthesis,2012,44(13):2 070-2 078.
© 2004-2018 中国地质图书馆版权所有 京ICP备05064691号 京公网安备11010802017129号 地址：北京市海淀区学院路29号 邮编：100083 电话：办公室：(+86 10)66554848；文献借阅、咨询服务、科技查新：66554700 |