Citation: Saisai Chen, Zhi Hong, Xiaoyu Huang, Xiaoqing Lv, Zongyang Li, Xinrou Hu, Xinying Ruan, Qianyan Yu. Syntheses of Dithiocarbamates Catalyzed by KF/nano-γ-Al₂O₃ under Microwave Irradiation[J]. Chemistry, ;2021, 84(6): 596-603. shu

Syntheses of Dithiocarbamates Catalyzed by KF/nano-γ-Al₂O₃ under Microwave Irradiation

School of Pharmaceutical and Materials Engineering, Taizhou University, Taizhou, 318000

Corresponding author: Zhi Hong, zhihong@tzc.edu.cn
Received Date: 16 December 2020
Accepted Date: 8 January 2021

Figures(5)

In this paper, an efficient method for the synthesis of dithiocarbamates under microwave irradiation condition with KF/nano-γ-Al₂O₃ catalyzed Michael addition of electron-deficient alkenes, amines and carbon disulfide in the PEG-400 solution was developed with yields of 76.5% to 91.6%. Meanwhile, the effects of the catalyst, solvent, microwave power, reaction time on the reaction were investigated, and the optimum conditions of the experiment were determined. This method has the advantages of short reaction time, high yield and environmental friendliness. In addition, KF/nano-γ-Al₂O₃ catalyzed one-pot synthesis of dithiocarbamates from benzaldehyde, ketones, amines and carbon disulfide in PEG-400 solution under microwave irradiation was investigated. The yields were 73.4%~82.8%.
- Dithiocarbamates,
- Microwave irradiation,
- Michael addition,
- KF/nano-γ-Al₂O₃
1. [1]
  Sperling J M, Warzecha E J, Celis-Barros C, et al. Nature, 2020, 583(7816): 396~399.
2. [2]
  Jiang S C, Su S J, Chen M, et al. J. Agric. Food Chem., 2020, 68(20): 5641~5647.
3. [3]
  Stasevych M, Zvarych V, Lunin V, et al. SAR QSAR Environ. Res., 2017, 28(5): 355~366.
4. [4]
  Altintop M D, Sever B, Akalin C G, et al. Eur. J. Med. Chem., 2017, 125(5): 190~196.
5. [5]
  Tangtrongsup S, Kisiday J D. Cell. Mol. Bioeng., 2019, 12(2): 153~163.
6. [6]
  Manar K K, Yadav C L, Tiwari N, et al. CrystEngComm, 2017(19): 2660~2672.
7. [7]
8. [8]
  Kartina D, Wahab A W, Ahmad A, et al. Sys. Rev. Pharm., 2020, 11(9): 43~51.
9. [9]
  Asadipour A, Shams Z, Eskandari K, et al. Res. Chem. Intermed., 2017, 44(2): 1295~1340.
10. [10]
11. [11]
  Quiroga D, Becerra L D, Coy-Barrera E. ACS Omega, 2019, 4(9): 13710~13720.
12. [12]
  Zhou S G, Wang J H, Zhang F F, et al. Org. Lett., 2016, 18(10): 2427~2430.
13. [13]
  Basavaiah D, Pal S, Veeraraghavaiah G, et al. Tetrahedron, 2015, 71(28): 4659~4664.
14. [14]
  Guo B G, Ge Z M, Cheng T M, et al. Synth. Commun., 2001, 31(19): 3021~3025.
15. [15]
  Xia S, Wang X, Ge Z M, et al. Tetrahedron, 2009, 65(5): 1005~1009.
16. [16]
  Vargas D F, L Larghi E, Kaufman T S. Synthesis, 2019, 51(9): 2030~2038.
17. [17]
  Kshiar B, Shangpliang O R, Myrboh B. Synthetic Commun., 2018, 48(14): 1816~1827.
18. [18]
  Tang Y, Ren H M, Chang F Q, et al. RSC Adv., 2017, 7(10): 5694~5700.
19. [19]
  Hong Z, Li J J, Chen G, et al. RSC Adv., 2016, 6(16): 13581~13588.
20. [20]
  Fridkin G, Yehezkel L, Columbus I, et al. J. Org. Chem., 2016, 81(5): 2154~2158.
21. [21]
  Gogoi P, Konwar D. Tetrahedron Lett., 2007, 48(4): 531~533.
22. [22]
  Fan M M, Liao D K, Aboud M F A, et al. Angew. Chem. Int. Ed., 2020, 59(21): 8247~8254.
23. [23]
24. [24]
  Buess C M. J. Am. Chem. Soc., 1955, 77(24): 6613~6615.
25. [25]
  Zhivotova T S, Gazaliev A M, Ibraev M K, et al. Russ. J. Appl. Chem., 2004, 77(8): 1321~1324.
26. [26]
  Schweiger K. Monatsh. Chem., 1980, 111(5): 1175~1184.
27. [27]
  Kreutzkamp N, Peschel H. Arch. Pharmaz., 1971, 304(7): 477~481.
28. [28]
  Bacharaju K, Jambula S R, Sivan S, et al. Bioorg. Med. Chem. Lett., 2012, 22(9): 3274~3277.
29. [29]
  Kalia S B, Puri R, Thakur A, et al. J. Therm. Anal. Calorim., 2015, 119(3): 1619~1632.
30. [30]
  Azizi N, Khajeh M, Hasani M, et al. Tetrahedron Lett., 2013, 54(39): 5407~5410.
31. [31]
  Fridkin G, Columbus I, Yehezkel L, et al. J. Org. Chem., 2018, 83(17): 10541~10545.
32. [32]
1. [1]
  Liuyun Chen , Wenju Wang , Tairong Lu , Xuan Luo , Xinling Xie , Kelin Huang , Shanli Qin , Tongming Su , Zuzeng Qin , Hongbing Ji . Soft template-induced deep pore structure of Cu/Al₂O₃ for promoting plasma-catalyzed CO₂ hydrogenation to DME. Acta Physico-Chimica Sinica, 2025, 41(6): 100054-0. doi: 10.1016/j.actphy.2025.100054
2. [2]
  Xiaorui Chen , Xuan Luo , Tongming Su , Xinling Xie , Liuyun Chen , Yuejing Bin , Zuzeng Qin , Hongbing Ji . Ga-doped Cu/γ-Al₂O₃ bifunctional interface sites promote the direct hydrogenation of CO₂ to DME. Acta Physico-Chimica Sinica, 2025, 41(10): 100126-0. doi: 10.1016/j.actphy.2025.100126
3. [3]
  Yanhui Guo , Li Wei , Zhonglin Wen , Chaorong Qi , Huanfeng Jiang . Recent Progress on Conversion of Carbon Dioxide into Carbamates. Acta Physico-Chimica Sinica, 2024, 40(4): 2307004-0. doi: 10.3866/PKU.WHXB202307004
4. [4]
  Haotian Zhang , Shengfa Feng , Mufan Cao , Xiong Xiong Liu , Pengcheng Yuan , Yaping Wang , Min Gao , Long Pan , Zhengming Sun . Al₂O₃ coated polyimide porous films enable thin yet strong polymer-in-salt solid-state electrolytes for dendrite-free lithium metal batteries. Chinese Chemical Letters, 2025, 36(8): 111096-. doi: 10.1016/j.cclet.2025.111096
5. [5]
  Zhiquan YIN , Wenlong ZHEN , Xiaofeng NING , Zhengzhi HAN , Gongxuan LÜ . Mechanism of Al₂O₃ layer in enhancing the stability and activity of GaN for photocatalytic overall water splitting. Chinese Journal of Inorganic Chemistry, 2026, 42(7): 1523-1533. doi: 10.11862/CJIC.20260038
6. [6]
  Qiang Wang , Jifan Yang , Xiaolei Su , Yi Liu . La₂O₃ decorated Ti₃C₂T_x MXene: temperature regulation and frequency selective surface synergy for enhanced X-Band microwave absorption. Acta Physico-Chimica Sinica, 2026, 42(8): 100308-0. doi: 10.1016/j.actphy.2026.100308
7. [7]
  Ruolin CHENG , Yue WANG , Xiyao NIU , Huagen LIANG , Ling LIU , Shijian LU . Efficient photothermal catalytic CO₂ cycloaddition over W₁₈O₄₉/rGO composites. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1276-1284. doi: 10.11862/CJIC.20240424
8. [8]
  Ruolin CHENG , Haoran WANG , Jing REN , Yingying MA , Huagen LIANG . Efficient photocatalytic CO₂ cycloaddition over W₁₈O₄₉/NH₂-UiO-66 composite catalyst. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 523-532. doi: 10.11862/CJIC.20230349
9. [9]
  Jiajia Li , Xiangyu Zhang , Zhihan Yuan , Zhengyang Qian , Jian Zhu . 3D Printing Based on Photo-Induced Reversible Addition-Fragmentation Chain Transfer Polymerization. University Chemistry, 2024, 39(5): 11-19. doi: 10.3866/PKU.DXHX202309073
10. [10]
  Bin XU , Shufeng ZHANG , Feifan LANG , Chunyan NI , Bing WU , Jianping LANG . Photoreactive pyrene-based Zn?? metal-organic frameworks: Solid-state [2+2] cycloaddition and tunable luminescence. Chinese Journal of Inorganic Chemistry, 2026, 42(10): 2119-2126. doi: 10.11862/CJIC.20260140
11. [11]
  Yujie WANG , Laobang WANG , Zheng ZHANG , Qi LIU , Jianping LANG . Construction of W/Cu/S cluster-based supramolecular compounds via alkynyl/sulfur cycloaddition and their third-order nonlinear optical properties. Chinese Journal of Inorganic Chemistry, 2025, 41(10): 2069-2077. doi: 10.11862/CJIC.20250129
12. [12]
  Tong TAO , Shufeng ZHANG , Feifan LANG , Chunyan NI , Bing WU , Jianping LANG . Synthesis, structures, and daylight-induced [2+2] cycloaddition reactivity of two Cd(Ⅱ)-based pillared-layer coordination polymers. Chinese Journal of Inorganic Chemistry, 2026, 42(6): 1121-1130. doi: 10.11862/CJIC.20260115
13. [13]
  Jinyang SUI , Zhonghao NIU , Hao XU , Jingli XIE . Zinc(Ⅱ) coordination polymers from mixed triazole and carboxylate ligands: Synthesis and properties for CO₂ cycloaddition and photocatalytic dye degradation. Chinese Journal of Inorganic Chemistry, 2026, 42(8): 1603-1612. doi: 10.11862/CJIC.20260089
14. [14]
  Jianding LI , Junyang FENG , Huimin REN , Gang LI . Proton conductive properties of a Hf(Ⅳ)-based metal-organic framework built by 2,5-dibromophenyl-4,6-dicarboxylic acid. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1094-1100. doi: 10.11862/CJIC.20240464
15. [15]
  Botao QU , Qian WANG , Qian WANG , Ruiping ZHANG . Synthesis, crystal structures, and luminescence properties of zinc coordination polymers based on 2,5-dibromoterephthalate. Chinese Journal of Inorganic Chemistry, 2026, 42(5): 917-924. doi: 10.11862/CJIC.20260357
16. [16]
  Shuai Zhang , Haifeng Li , Shijie Zhang , Shun Wang , Suxuan Du , Zhiwei Zhao , Xiaomiao Zhao , Xiaowei Liang . Microwave assisted construction of Ta₂CT_x MXene/CuInS₂ heterostructures toward enhanced dielectric loss and broadband electromagnetic wave absorption. Acta Physico-Chimica Sinica, 2026, 42(8): 100305-0. doi: 10.1016/j.actphy.2026.100305
17. [17]
  Min LI , Xianfeng MENG . Preparation and microwave absorption properties of ZIF-67 derived Co@C/MoS₂ nanocomposites. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1932-1942. doi: 10.11862/CJIC.20240065
18. [18]
  Haotong Ma , Mingyu Heng , Yang Xu , Wei Bi , Yingchun Miao , Shuning Xiao . Synergistic carbon doping and Cu loading on boron nitride via microwave synthesis for enhanced atmospheric CO₂ photoreduction. Acta Physico-Chimica Sinica, 2025, 41(11): 100132-0. doi: 10.1016/j.actphy.2025.100132
19. [19]
  Shuhao FENG , Feibing XIONG , Yaqing LIN , Han SU , Xu HAN . Preparation and luminescent properties of alkaline metal doped Cd₃Al₂Ge₃O₁₂: Pr³⁺ orange phosphors. Chinese Journal of Inorganic Chemistry, 2026, 42(2): 284-296. doi: 10.11862/CJIC.20250171
20. [20]
  Wei Li , Guoqiang Feng , Ze Chang . Teaching Reform of X-ray Diffraction Using Synchrotron Radiation in Materials Chemistry. University Chemistry, 2024, 39(3): 29-35. doi: 10.3866/PKU.DXHX202308060

Get Citation

PDF

XML

Metrics

PDF Downloads(22)
Abstract views(7619)
HTML views(1052)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

Syntheses of Dithiocarbamates Catalyzed by KF/nano-γ-Al2O3 under Microwave Irradiation

Metrics

通讯作者: 陈斌, bchen63@163.com

Syntheses of Dithiocarbamates Catalyzed by KF/nano-γ-Al₂O₃ under Microwave Irradiation