超声辐射下水溶液中离子液体催化合成芳醛缩氨基硫脲

doi:10.3969/j.issn.1000-1565.2013.04.008

摘要/Abstract

摘要： 在超声波辐射下水相中以酸性甲基咪唑丙烷磺酸-三氟乙酸离子液体催化芳醛和氨基硫脲进行反应,合成了系列芳醛缩氨基硫脲衍生物,产率为60.0％～95.0％.产物结构经1 HNMR,IR,元素分析表征,该反应具有反应时间短、产率高、环境友好、后处理方便、催化剂可回收重复使用的优点.

关键词: 超声波辐射, 离子液体, 催化, 缩氨基硫脲

Key words: ultrasound irradiation, ionic liquid, catalysis, thiosemicarbazones

中图分类号:

O623.6

刘卉闵,崔鹏雷,魏俊萍,张冬暖,张英群. 超声辐射下水溶液中离子液体催化合成芳醛缩氨基硫脲[J]. 河北大学学报(自然科学版), 2013, 33(4): 375-379.

LIU Huimin,CUI Penglei,WEI Junping,ZHANG Dongnuan,ZHANG Yingqun. Synthesis of aromatic aldehyde thiosemicarbazones catalyzed by ionic liquid in water under ultrasound irradiation[J]. Journal of Hebei University (Natural Science Edition), 2013, 33(4): 375-379.

参考文献

[1] 王建华, 杜军, WANG Jian-Hua, DU Jun. 2, 4-二羟基苯乙酮缩氨基硫脲及其金属配合物的合成与性质 [J]. 无机化学学报 1999.doi:10.3321/j.issn:1001-4861.1999.05.020
[2] 李明, 刘利军, 戴小军, 冉旭辉, 李淑娟, LI Ming, LIU Li-jun, DAI Xiao-jun, RAN Xu-hui, LI Shu-juan. 取代苯甲醛缩氨基硫脲的合成方法研究 [J]. 宁夏工程技术 2007.doi:10.3969/j.issn.1671-7244.2007.04.014
[3] 施小宁, 樊娟, SHI Xiao-ning, FAN Juan. 超声辐射水溶液中取代芳醛、芳酮缩氨基硫脲的合成 [J]. 宝鸡文理学院学报（自然科学版） 2008.doi:10.3969/j.issn.1007-1261.2008.01.009
[4] 王振, 董玮, 徐焱, 梁沛, 杨新玲, WANG Zhen, DONG Wei, XU Yan, LIANG Pei, YANG Xin-ling. 取代苯甲醛缩氨基硫脲(脲、硝基胍)类化合物的合成及其对小菜蛾酪氨酸酶的抑制活性 [J]. 农药学学报 2010.doi:10.3969/j.issn.1008-7303.2010.03.04
[5] 解先业, 姜林, 薛超彬, 罗万春, XIE Xian-ye, JIANG Lin, XUE Chao-bin, LUO Wan-chun. 取代苯甲醛缩氨基硫脲的合成及其对昆虫酚氧化酶的抑制活性 [J]. 化学试剂 2007.doi:10.3969/j.issn.0258-3283.2007.01.010
[6] Hu WX, Zhou W, Xia CN, Wen X. Synthesis and anticancer activity of thiosemicarbazones. [J]. Bioorganic and Medicinal Chemistry Letters 2006, 8(8).
[7] Shih MH, Wu CL. Efficient syntheses of thiadiazoline and thiadiazole derivatives by the cyclization of 3-aryl-4-formylsydnone thiosemicarbazones with acetic anhydride and ferric chloride [J]. Tetrahedron 2005, 46(46).
[8] Sriram D, Yogeeswari P, Thirumurugan R, Pavana RK. Discovery of new antitubercular oxazolyl thiosemicarbazones [J]. Journal of Medicinal Chemistry 2006, 12(12).
[9] Cukurovali A, Yilmaz I, Gur S, Kazaz C. Synthesis, antibacterial and antifungal activity of some new thiazolylhydrazone derivatives containing 3-substituted cyclobutane ring. [J]. European Journal of Medicinal Chemistry: Chimie Therapeutique 2006, 2(2).
[10] Pavan FR, da S Maia PI, Leite SR, Deflon VM, Batista AA, Sato DN, Franzblau SG, Leite CQ. Thiosemicarbazones, semicarbazones, dithiocarbazates and hydrazide/hydrazones: anti-Mycobacterium tuberculosis activity and cytotoxicity. [J]. European Journal of Medicinal Chemistry 2010, 5(5).
[11] 周毓萍, 杨正银, 于红娟. 1-苯基-3-甲基-4-苯甲酰基吡唑酮-5-缩氨基硫脲稀土配合物的合成, 表征及抑菌活性 [J]. 应用化学 1999.
[12] Ana Cristina Lima Leite, Diogo Rodrigo de M.Moreira, Lucas Cunha Duarte Coelho. Synthesis of aryl-hydrazones via ultrasound irradiation in aqueous medium [J]. Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry 2008, 9(9).
[13] M. H. Entezari, A. A. Shameli. Phase-transfer catalysis and ultrasonic waves I. Cannizzaro reaction [J]. Ultrasonics sonochemistry 2000, 4(4).
[14] GAPLOVSKY A, DONOVALOVA J, TOMA S. Ultrasound effects on photochemical reactions, Part 1:photochemical reactions of ketones with alkenes [J]. Ultrasonics Sonochemistry 1997, 4(02).
[15] Ross NA., MacGregor RR., Bartsch RA.. Synthesis of beta-lactams and beta-aminoesters via high intensity ultrasound-promoted Reformatsky reactions [J]. Tetrahedron 2004, 9(9).
[16] A. Tuulmets, P. Raik. Ultrasonic acceleration of ester hydrolyses [J]. Ultrasonics sonochemistry 1999, 1/2(1/2).
[17] KUMAR V G, KIM K 13. Organized and highly dispersed growth of MnO2 nano-rods by sonochemical hydrolysis of Mn (3)acetate ultrason [J]. Sonochem 2006, 13(06).
[18] Zhang, L, Xian, M, He, YC, Li, LZ, Yang, JM, Yu, ST, Xu, X. A Bronsted acidic ionic liquid as an efficient and environmentally benign catalyst for biodiesel synthesis from free fatty acids and alcohols [J]. Bioresource Technology: Biomass, Bioenergy, Biowastes, Conversion Technologies, Biotransformations, Production Technologies 2009, 19(19).
[19] PUEZER B, HAMLIN W E, KATZ L. A Preparative method for thiosemicarbazones of aromatic aldehydes [J]. Journal of the American Chemical Society 1951, 73(06).
[20] 刘建宁, 董彦杰, 于新桥. 2, 4-二氯苯甲醛缩氨基硫脲Cu(Ⅰ), Fe(Ⅱ), Zn(Ⅱ)配合物的直接电化学合成 [J]. 阜阳师范学院学报(自然科学版) 1999, 16(01).