(4-咔唑-9-基-苯亚甲基)-(5-咔唑-9-亚甲基-[1,3,4]噻二唑-2-基)-胺的合成与表征
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摘要
以咔唑、氯乙酸和硫代氨基脲为原料,经亲核取代、闭环反应合成了5-咔唑-9-亚甲基-2-氨基-1,3,4-噻二唑。同时,以咔唑和对氯苯甲醛为原料,在碱性催化剂条件下,在DMF溶液中回流反应得到4-咔唑-9基苯甲醛。两者通过固相研磨的合成方法得到新化合物(4-咔唑-9-基-苯亚甲基)-(5-咔唑-9-亚甲基-[1,3,4]噻二唑-2-基)-胺。通过单因素法对(4-咔唑-9-基-苯亚甲基)-(5-咔唑-9-亚甲基-[1,3,4]噻二唑-2-基)-胺的合成条件进行探讨,确定了合成该化合物的最佳反应条件:反应物物质的量比为1∶1∶1.2,反应时间为20min。其结构经IR、1HNMR、UV-vis和元素分析进行表征。
2-amino-5-( N-Carbazolyl methylene)-1,3,4-thiadiazole was compounded with carbazole、chloroacetic acid and thiosemicarbazide under nucleophilic substitution and closed-loop reaction.The compound 4-(9H-Carbazol-9-yl) benzaldehyde was prepared by carbazole with 4-chlorobenzaldehyde under refluxing by the catalysis of alkaline catalyst. At the same time, the new compound(4-carbazole-9-yl-benzomethylene)-(5-carbazole-9-methylene-[1,3,4] thiadiazole-2-yl) amine was synthesized by 4-(9H-Carbazol-9-yl) benzaldehyde with 2-amino-5-(N-Carbazolyl methylene)-1,3,4-thiadiazole through solvent-free solid phase grinding method. The factors that influences on product yield were discussed by single factor method. The result that appropriate reaction conditions are as follows: molar ratio of reactants was 1∶1∶1.2, the reaction time was 20 minutes. The product was characterized by IR., 1H NMR UV-Vis and ele mental analysis.
2-amino-5-( N-Carbazolyl methylene)-1,3,4-thiadiazole was compounded with carbazole、chloroacetic acid and thiosemicarbazide under nucleophilic substitution and closed-loop reaction.The compound 4-(9H-Carbazol-9-yl) benzaldehyde was prepared by carbazole with 4-chlorobenzaldehyde under refluxing by the catalysis of alkaline catalyst. At the same time, the new compound(4-carbazole-9-yl-benzomethylene)-(5-carbazole-9-methylene-[1,3,4] thiadiazole-2-yl) amine was synthesized by 4-(9H-Carbazol-9-yl) benzaldehyde with 2-amino-5-(N-Carbazolyl methylene)-1,3,4-thiadiazole through solvent-free solid phase grinding method. The factors that influences on product yield were discussed by single factor method. The result that appropriate reaction conditions are as follows: molar ratio of reactants was 1∶1∶1.2, the reaction time was 20 minutes. The product was characterized by IR., 1H NMR UV-Vis and ele mental analysis.
引文
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[12] Guo Dong-Cai, Ping-Liang, et al.Synthesis and characterization of six new carbazolyl porphyrins[J]. Synthetic Communications, 2010, 40(22):3315-3321.
[13] Hemlata Kaur, Sunil Kumar, Pinki Vishwakarma, et al. Synthesis and antipsychotic and anticonvulsant activity of some new substituted oxa/thiadiazolylazetidinonyl/thiazolidinonyl carbazoles[J]. European Journal of Medicinal Chemistry, 2010,45:2777-2783.
[14] Yang Lifen, Guan Min, Bian, et al. Synthesis, characterization,photophysics and electroluminescence based on a series of pyran-containing emitters[J]. Thin Solid Films, 2006, 500:224-230.
[2] Nadia Salih, Jumat Salimon, Emad Yousif. Synthesis and antimicrobial activities of 9H-carbazole derivatives[J]. Arabian Journal of Chemistry, 2011, 1-6.
[3]王中原,孙思远,薛松.一种咔唑衍生物的合成与表征[J].天津理工大学学报, 2010, 26(4):1-3.
[4]崔慧玲,王丽红,白官,等. N-氨基咔唑合成的研究[J].应用化工, 2006, 35(4):295-297.
[5] Matias Mon?alves, Daniel da Silveira Rampon, Paulo Henrique Schneider, et al. Divinyl sulfides/sulfones-based D-π-A-π-D dyes as efficient non-aromatic bridges forπ-conjugated compounds[J]. Dyes and Pigments, 2014, 102:71-78.
[6] Hemlata Kaur, Sunil Kumar, Pinki Vishwakarma, et al. Synthesis and antipsychotic and anticonvulsant activity of some new substituted oxa/thiadiazolylazetidinonyl/thiazolidinonyl carbazoles[J]. European Journal of Medicinal Chemistry, 2010, 45:2777-2783.
[7] Zhaohui Wang, Kongchang, Chen, He Tian. Synthesis and Electrochemical Properties of lntramolecular Multi-electron Transfer Probe Compounds[J]. DyesandPigments, 1996, 30(4):261-269.
[8] Wusheng Ren, Hao Zhuang, Qing Bao, et al. Enhancing the coplanarity of the donor moiety in a donor-acceptor molecule to improve the ef ciency of switching phenomenon for ash memory devices[J]. Dyes and Pigments, 2014, 100:127-134.
[9]朱维菊,李村,吴振玉,等.一种新型长共轭结构咔唑衍生物的合成及其光学性质[J].合成化学, 2010, 18(6):718-720.
[10]彭化男,郑大贵,谢嘉霖,等.一种新型不对称咔唑衍生物的合成和光电性能[J].化学试剂, 2013, 35(2):121-123.
[11]卞垒,曾向潮,何如,罗创龙.含咔唑基苯并咪唑衍生物的合成[J].有机化学.2014,34:994-998.
[12] Guo Dong-Cai, Ping-Liang, et al.Synthesis and characterization of six new carbazolyl porphyrins[J]. Synthetic Communications, 2010, 40(22):3315-3321.
[13] Hemlata Kaur, Sunil Kumar, Pinki Vishwakarma, et al. Synthesis and antipsychotic and anticonvulsant activity of some new substituted oxa/thiadiazolylazetidinonyl/thiazolidinonyl carbazoles[J]. European Journal of Medicinal Chemistry, 2010,45:2777-2783.
[14] Yang Lifen, Guan Min, Bian, et al. Synthesis, characterization,photophysics and electroluminescence based on a series of pyran-containing emitters[J]. Thin Solid Films, 2006, 500:224-230.