[1]王亮,潘亮,陈群,等.酸性离子交换树脂催化4-芳基-1H-1,2,3-三唑的合成[J].常州大学学报(自然科学版),2017,(04):1-6.[doi:10.3969/j.issn.2095-0411.2017.04.001]
 WANG Liang,PAN Liang,CHEN Qun,et al.Acidic Ion-Exchange Resin-Catalyzed Synthesis of 4-Aryl-1H-1,2,3-Triazoles[J].Journal of Changzhou University(Natural Science Edition),2017,(04):1-6.[doi:10.3969/j.issn.2095-0411.2017.04.001]
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酸性离子交换树脂催化4-芳基-1H-1,2,3-三唑的合成()
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常州大学学报(自然科学版)[ISSN:2095-0411/CN:32-1822/N]

卷:
期数:
2017年04期
页码:
1-6
栏目:
化学化工
出版日期:
2017-07-30

文章信息/Info

Title:
Acidic Ion-Exchange Resin-Catalyzed Synthesis of 4-Aryl-1H-1,2,3-Triazoles
作者:
王亮潘亮陈群何明阳
常州大学 石油化工学院,江苏 常州 213164
Author(s):
WANG Liang PAN Liang CHEN Qun HE Mingyang
School of Petrochemical Engineering, Changzhou University, Changzhou 213164, China
关键词:
4-芳基-1H-123-三唑 酸性离子交换树脂 硝基烯烃 叠氮化钠
Keywords:
4-aryl-1H-123-triazole acidic ion-exchange resin nitroolefins sodium azide
分类号:
O 621.3
DOI:
10.3969/j.issn.2095-0411.2017.04.001
文献标志码:
A
摘要:
以酸性离子交换树脂Amberlite IR-120为催化剂,硝基烯烃和叠氮化钠为原料合成了一系列4-芳基-1H-1,2,3-三唑衍生物。与常规方法相比,该法高效、反应条件温和且底物兼容性好。另外,催化剂通过过滤即可实现回收,重复使用6次后活性略有降低。
Abstract:
A series of 4-aryl-1H-1,2,3-triazole derivatives were synthesized by 1,3-dipolar cycloaddition of nitroolefins with NaN3 using Amberlite IR-120 resin as the catalyst. Compared with conventional methods, good efficiency, mild reaction conditions and good substrate compatibility are the major advantages of the present protocol. In addition, the catalyst can be easily recovered by filtration, and can be reused for successive six runs with slight decrease in its activity.

参考文献/References:

[1] THIRUMURUGAN P, MATOSIUK D, JOZWIAK K. Click chemistry for drug development and diverse chemical-biology applications[J]. Chem Rev, 2013, 113(7): 4905-4979.
[2]LAU Y, RUTLEDGE P, WATKINSON M, et al. Chemical sensors that incorporate click-derived triazoles[J]. Chem Soc Rev, 2011, 40(5): 2848-2866.
[3]LIU Y, ZHANG L, XU X, et al. Intramolecular C-H…F hydrogen bonding-induced 1,2,3-triazole-based foldamers[J]. Org Chem Front, 2014, 1(5): 494-500.
[4]TOTOBENAZARA J, BURKE A J. New click-chemistry methods for 1,2,3-triazoles synthesis: recent advances and applications[J]. Tetrahedron Lett, 2015, 56(22): 2853-2859.
[5]梁翠荣,金桂花,吴胜楠,等. 点击化学应用于合成1,2,3-三唑衍生物的研究进展[J]. 常州大学学报(自然科学版),2015,27(1):54-61.
[6]KOLB H C, FINN M G, SHARPLESS K B. Click chemistry: diverse chemical function from a few good reactions[J]. Angew Chem Int Ed, 2001, 40(11):2004-2021.
[7]ROSTOVTSEV V V, GREEN L G, FOKIN V V, et al. A stepwise Huisgen cycloaddition process: copper(I)-catalyzed regioselective “ligation” of azides and terminal alkynes[J]. Angew Chem Int Ed, 2002, 41(14): 2596-2599.
[8]HEIN J E, TRIPP J C, KRASNOVA L B, et al. Copper(I)-catalyzed cycloaddition of organic azides and 1-iodoalkynes[J]. Angew Chem Int Ed, 2009, 48(43): 8018-8021.
[9]ZHANG L, CHEN X G, XUE P, et al. Ruthenium-catalyzed cycloaddition of alkynes and organic azides[J]. J Am Chem Soc, 2005, 127(46): 15998-15999.
[10]RAMACHARY D B, SHASHANK A B. Organocatalytic triazole formation, followed by oxidative aromatization: regioselective metal-free synthesis of benzotriazoles[J]. Chem Eur J, 2013, 19(39): 13175-13181.
[11]LI W, DU Z, HUANG J, et al. Direct access to 1,2,3-triazoles through organocatalytic 1,3-dipolar cycloaddition reaction of allyl ketones with azides[J]. Green Chem, 2014, 16(6): 3003-3006.
[12]CHEN Z, YAN Q, LIU Z, et al. Copper-mediated synthesis of 1,2,3-triazoles from N-tosylhydrazones and anilines[J]. Angew Chem Int Ed, 2013, 52(50): 13324-13328.
[13]YAN W, WANG Q, CHEN Y, et al. Iron-catalyzed C-O bond activation for the synthesis of propargyl-1,2,3-triazoles and 1,1-bis-triazoles[J]. Org Lett, 2010, 12(15): 3308-3311.
[14]JIN T, 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): 3789-3791.
[15]WANG X, KUANG C, YANG Q. Copper-catalyzed synthesis of 4-aryl-1H-1,2,3-triazoles from 1,1-dibromoalkenes and sodium azide[J]. Eur J Org Chem, 2012(2): 424-428.
[16]QUAN X, REN Z, WANG Y, et al. p-Toluenesulfonic acid mediated 1,3-dipolar cycloaddition of nitroolefins with NaN3 for synthesis of 4-aryl-NH-1,2,3-triazoles[J]. Org Lett, 2014, 16(21): 5728-5731.
[17]GAIRAUD C B, LAPPIN G R. The synthesis of ω-nitrostyrenes[J]. J Org Chem, 1953, 18(1): 1-3.
[18]ZEFIROV N S, CHAPOVSKAYA N K, KOLESNIKOV V V. Synthesis of 1,2,3-triazoles by reaction of azide ion with α,β-unsaturated nitro-compounds and nitriles[J]. J Chem Soc D, 1971(17): 1001-1002.

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备注/Memo

备注/Memo:
收稿日期:2016-09-09。基金项目:国家自然科学基金资助项目(21302014)。作者简介:王亮(1984—),男,江苏常州人,博士,副教授,主要从事有机合成方法学研究。通讯联系人:何明阳(1962—),E-mail: hemingyangjpu@yahoo.com
更新日期/Last Update: 2017-07-20