硫酸铜/取代硫脲水相中高效催化合成N-磺酰基三氮唑
|
摘要
利用系列含磺酰基的叠氮化物与末端炔反应,制备了N-磺酰基三氮唑化合物.研究结果表明,硫酸铜/取代硫脲的组合不仅适用于一般的铜催化叠氮端炔环加成(Cu AAC)反应,还可以在水相中高效催化合成N-磺酰基-1,2,3-三氮唑.这类反应对水不敏感,在水相中的反应产率高达99%,且在空气中室温(25℃)下搅拌即可进行.该方法反应条件温和、绿色环保、成本低、底物普适性广且反应效率高.
The reaction of a series of sulfonyl-containing azides and terminal alkynes indicated that the combination of copper sulfate/substituted thiourea was more suitable for general copper-catalyzed azide-end alkyne ring addition[Cu(Ⅰ) catalyzed azide-alkyne cycloaddition,CuAAC]reaction. The type of reaction was also possible to efficiently catalyze the synthesis of N-sulfonyl-1,2,3-triazole in the aqueous phase. The type of reaction was not sensitive to water and the yield was up to 99% in the aqueous phase. The reaction mixture was stirred in the air under room temperature(25 ℃). The novel system showed high atom-economy and functional-group tolurance. It provided a simple and efficient synthesis method for the synthesis of a series of N-sulfonyltriazoles.
The reaction of a series of sulfonyl-containing azides and terminal alkynes indicated that the combination of copper sulfate/substituted thiourea was more suitable for general copper-catalyzed azide-end alkyne ring addition[Cu(Ⅰ) catalyzed azide-alkyne cycloaddition,CuAAC]reaction. The type of reaction was also possible to efficiently catalyze the synthesis of N-sulfonyl-1,2,3-triazole in the aqueous phase. The type of reaction was not sensitive to water and the yield was up to 99% in the aqueous phase. The reaction mixture was stirred in the air under room temperature(25 ℃). The novel system showed high atom-economy and functional-group tolurance. It provided a simple and efficient synthesis method for the synthesis of a series of N-sulfonyltriazoles.
引文
[1] Thirumurugan P.,Matosiuk D.,Jozwiak K.,Chem. Rev.,2013,113(7),4905—4979
[2] Burakowska E.,Quinn J. R.,Zimmerman S. C.,Haag R.,J. Am. Chem. Soc.,2009,131(30),10574—10580
[3] Ghio S.,Constantin C.,Klersy C.,Serio A.,Fontana A.,Campana C.,Eur. Heart J.,2004,25(7),571—578
[4] De J. H.,Abbaspour K. T.,Maes B. U.,Angew. Chem. Int. Edit.,2012,124(11),2799—2802
[5] Takeshi O.,Masato S.,Akira M.,Kenji S.,Tomohiko U.,Teruaki U.,Hiroshi T.,Kazuya M.,Yoshiaki T.,Bioorg. Med. Chem. Lett.,2005,15(4),1055—1059
[6] Sripathi S.,Reddy R. B.,Karnati V. R.,Raju V. V. N. K. V. P.,Khunt M. D.,Org. Process Res. Dev.,2008,13(4),804—806
[7] Song I.,Borland J.,Chen S.,Guta P.,Lou Y.,Wilfret D.,Pharmacol.,2014,70(10),1173—1179
[8] Bianchini C.,Mantovani G.,Meli A.,Migliacci F.,Zanobini F.,Laschi F.,Sommazzi A.,Eur. J. Inorg. Chem.,2003,1620—1631
[9] Ning Z.,Zhang Q.,Wu W. J.,He T.,J. Organomet. Chem.,2009,694(17),2705—2711
[10] Yang J. Q.,Wu G. J.,He Y. P.,Han F. S.,Chem. Res. Chinese Universities,2018,34(5),727—731
[11] Zhang Y. C.,Wen C. X.,Zhang C. J.,Li J. Z.,Chem. Res. Chinese Universities,2018,34(4),552—558
[12] Lutz J. F.,Brner H. G.,Weichenhan K.,Macromol. Rapid Comm.,2005,26(7),514—518
[13] Sumerlin B. S.,Tsarevsky N. V.,Louche G.,Lee R. Y.,Macromolecules,2005,38(18),7540—7545
[14] Morten M.,Christian W. T.,Chem. Rev.,2008,108(8),2952—3015
[15] Xiong X. Q.,Cai L.,Tang Z. K.,Chin. J. Org. Chem.,2012,32(8),1410—1428(熊兴泉,蔡雷,唐忠科.有机化学,2012,32(8),1410—1428)
[16] Kolb H. C.,Sharpless K. B.,Drug Discovery Today,2003,8(24),1128—1137
[17] Rostovtsev V. V.,Green L. G.,Fokin V. V.,Cheminform,2002,33(43),2596—2599
[18] Torne C. W.,Christensen C.,Meldal M.,Eur. J. Org. Chem.,2002,67(9),3057—3064
[19] Cano I.,Nicasio M. C.,Pérez P. J.,Org. Biomol. Chem.,2010,8(3),536—538
[20] Fujioka H.,Murai K.,Ohba Y.,Hiramatsu A.,Kita Y.,Tetrahedron Lett.,2005,46(13),2197—2199
[21] Rao H.,Sawant A. A.,Tanpure A. A.,Chem. Commun.,2011,48(4),498—500
[22] Wang S.,Jia K.,Cheng J.,Tetrahedron Lett.,2017,58(38),3717—3721
[23] Seiju K.,Kisako H.,Hemant K. M.,Kouhei T.,Masayuki U.,Masayuki S.,Hiroshi T.,Chem. Pharm. Bull.,1985,33(2),662—666
[24] Li Y.,Feng Y.,Xu L.,Org. Lett.,2016,18(19),4924—4927
[25] Raushel J.,Pitram S. M.,Fokin V. V.,Org. Lett.,2008,10(16),3385—3388
[26] Wang L.,Yang Z.,Yang M.,Zhang R. Y.,Kuaia C. S.,Cui X. L.,Org. Biomol. Chem.,2017,15(39),8302—8307
[27] Raushel J.,Fokin V. V.,Org. Lett.,2010,12(21),4952—4955
[28] Miura T.,Fujimoto F.,Funakoshi Y.,Angew. Chem.,2015,127(34),10105—10108
[29] Liu Y.,Wang X.,Xu J.,Zhang Q.,Zhao Y.,Hu Y.,Tetrahedron Lett.,2011,67(34),6294—6299
[30] Ran R. Q.,He J.,Xiu S. D.,Wang K. B.,Li C. Y.,Org. Lett.,2014,16(14),3704—3707
[31] Li L. H.,Jiang Y.,Hao J.,Wei Y.,Shi M.,Adv. Synth. Catal.,2017,359(19),3304—3310
[2] Burakowska E.,Quinn J. R.,Zimmerman S. C.,Haag R.,J. Am. Chem. Soc.,2009,131(30),10574—10580
[3] Ghio S.,Constantin C.,Klersy C.,Serio A.,Fontana A.,Campana C.,Eur. Heart J.,2004,25(7),571—578
[4] De J. H.,Abbaspour K. T.,Maes B. U.,Angew. Chem. Int. Edit.,2012,124(11),2799—2802
[5] Takeshi O.,Masato S.,Akira M.,Kenji S.,Tomohiko U.,Teruaki U.,Hiroshi T.,Kazuya M.,Yoshiaki T.,Bioorg. Med. Chem. Lett.,2005,15(4),1055—1059
[6] Sripathi S.,Reddy R. B.,Karnati V. R.,Raju V. V. N. K. V. P.,Khunt M. D.,Org. Process Res. Dev.,2008,13(4),804—806
[7] Song I.,Borland J.,Chen S.,Guta P.,Lou Y.,Wilfret D.,Pharmacol.,2014,70(10),1173—1179
[8] Bianchini C.,Mantovani G.,Meli A.,Migliacci F.,Zanobini F.,Laschi F.,Sommazzi A.,Eur. J. Inorg. Chem.,2003,1620—1631
[9] Ning Z.,Zhang Q.,Wu W. J.,He T.,J. Organomet. Chem.,2009,694(17),2705—2711
[10] Yang J. Q.,Wu G. J.,He Y. P.,Han F. S.,Chem. Res. Chinese Universities,2018,34(5),727—731
[11] Zhang Y. C.,Wen C. X.,Zhang C. J.,Li J. Z.,Chem. Res. Chinese Universities,2018,34(4),552—558
[12] Lutz J. F.,Brner H. G.,Weichenhan K.,Macromol. Rapid Comm.,2005,26(7),514—518
[13] Sumerlin B. S.,Tsarevsky N. V.,Louche G.,Lee R. Y.,Macromolecules,2005,38(18),7540—7545
[14] Morten M.,Christian W. T.,Chem. Rev.,2008,108(8),2952—3015
[15] Xiong X. Q.,Cai L.,Tang Z. K.,Chin. J. Org. Chem.,2012,32(8),1410—1428(熊兴泉,蔡雷,唐忠科.有机化学,2012,32(8),1410—1428)
[16] Kolb H. C.,Sharpless K. B.,Drug Discovery Today,2003,8(24),1128—1137
[17] Rostovtsev V. V.,Green L. G.,Fokin V. V.,Cheminform,2002,33(43),2596—2599
[18] Torne C. W.,Christensen C.,Meldal M.,Eur. J. Org. Chem.,2002,67(9),3057—3064
[19] Cano I.,Nicasio M. C.,Pérez P. J.,Org. Biomol. Chem.,2010,8(3),536—538
[20] Fujioka H.,Murai K.,Ohba Y.,Hiramatsu A.,Kita Y.,Tetrahedron Lett.,2005,46(13),2197—2199
[21] Rao H.,Sawant A. A.,Tanpure A. A.,Chem. Commun.,2011,48(4),498—500
[22] Wang S.,Jia K.,Cheng J.,Tetrahedron Lett.,2017,58(38),3717—3721
[23] Seiju K.,Kisako H.,Hemant K. M.,Kouhei T.,Masayuki U.,Masayuki S.,Hiroshi T.,Chem. Pharm. Bull.,1985,33(2),662—666
[24] Li Y.,Feng Y.,Xu L.,Org. Lett.,2016,18(19),4924—4927
[25] Raushel J.,Pitram S. M.,Fokin V. V.,Org. Lett.,2008,10(16),3385—3388
[26] Wang L.,Yang Z.,Yang M.,Zhang R. Y.,Kuaia C. S.,Cui X. L.,Org. Biomol. Chem.,2017,15(39),8302—8307
[27] Raushel J.,Fokin V. V.,Org. Lett.,2010,12(21),4952—4955
[28] Miura T.,Fujimoto F.,Funakoshi Y.,Angew. Chem.,2015,127(34),10105—10108
[29] Liu Y.,Wang X.,Xu J.,Zhang Q.,Zhao Y.,Hu Y.,Tetrahedron Lett.,2011,67(34),6294—6299
[30] Ran R. Q.,He J.,Xiu S. D.,Wang K. B.,Li C. Y.,Org. Lett.,2014,16(14),3704—3707
[31] Li L. H.,Jiang Y.,Hao J.,Wei Y.,Shi M.,Adv. Synth. Catal.,2017,359(19),3304—3310