Citation: . Efficient One-Pot Synthesis of Diphenyl-2,4-dioxa-8,10-diazaspiro-[5.5]undecane-1,5,9-trione Derivatives under Solvent-Free and Catalyst-Free[J]. Chinese Journal of Organic Chemistry, ;2016, 36(8): 1948-1953. doi: 10.6023/cjoc201601032 shu

Efficient One-Pot Synthesis of Diphenyl-2,4-dioxa-8,10-diazaspiro-[5.5]undecane-1,5,9-trione Derivatives under Solvent-Free and Catalyst-Free

^a,*,, ,
^b ,
^a ,
^a ,
^c,*,, ,
^d ,
^c ,
^c

Corresponding author: , gotoxzh@163.com , gotoxzh@163.com
Received Date: 23 January 2016
Revised Date: 22 March 2016

Fund Project: the Graduate Innovation Foundation of Jiangxi Province No.YC2015-B023the National Natural Science Foundation of China Nos. 20566004

Figures(2)

Twelve kinds of diphenyl-2,4-dioxa-8,10-diazaspiro[5.5]undecane-1,5,9-trione derivatives were synthesized by the three-component one-pot reaction of aromatic aldehydes with urea and 2,2-butylidene-1,3-dioxane-4,6-dione or 2,2-pentyli- dene-1,3-dioxane-4,6-dione under solvent-free and catalyst-free. The yields ranged from 49% to 63%. Its advantages were no solvent pollution and mild reaction conditions. Furthermore, a proposed reaction mechanism for this condensation reaction was speculated and the relationship between reaction speed and substituent groups was also described. All the compounds synthesized were confirmed by ¹H NMR, ¹³C NMR, ESI-MS and IR techniques.
- three-component reaction,
- diphenyl-2,4-dioxa-8,10-diazaspiro[5.5]undecane-1,5,9-trione derivatives,
- solvent- free,
- catalyst-free
1. [1]
  Arimoto, H.; Hayakawa, I.; Kuramoto, M.; Uemure, D. Tetrahedron Lett. 1998, 39, 861.
2. [2]
  Chou, T.; Kuramoto, M.; Otani, Y.; Shkano, M.; Yazawa, K.; Uemere, D. Tetrahedron Lett. 1996, 37, 3867.
3. [3]
  Rovnyak, G. C.; Kimball, S. D.; Barbara, B.; Gabriella, C.; John, D. D.; Jack, G.; Anders, H.; Mary, M.; James P. M. J. Med. Chem. 1995, 38, 119.
4. [4]
  Snider, B. B.; Shi, Z. J. Org. Chem. 1993, 58, 3828.
5. [5]
  Wessjohann, L. A.; Rivera, D. G.; Vercillo, O. E. Chem. Rev. 2009, 109, 796.
6. [6]
7. [7]
  Yang, K.; Xiang, J. B.; Bao, G. C.; Dang, Q.; Bai, X. ACS Comb. Sci. 2013, 15, 519.
8. [8]
  Dipak, P.; Debajyoti, B.; Mukut, G.; Hu, W. H. Mol. Divers. 2011, 15, 257.
9. [9]
  Srinivasa, R. J.; Divya, V.; Shubha, J. J. Chem. Pharm. Res. 2012, 4, 2373.
10. [10]
  Zhu, Y. L.; Huang, S. L.; Pan, Y. J. Eur. J. Org. Chem. 2005, 2354.
11. [11]
  Laishram, R. D.; Okram, M. S. Indian J. Chem. 2012, 51B, 1426.
12. [12]
  Anil, S.; Sanjay, K.; Jagir S. S. Indian J. Chem., 2004, 43B, 2482.
13. [13]
14. [14]
  Naser, M.; Khalil, P.; Masoud, B.; Soudabeh, K. Asian J. Chem. 2013, 25, 3373.
15. [15]
  Wang, R.; Liu, Z. Q. J. Org. Chem. 2012, 77, 3952.
16. [16]
  Laurence, C.; Loïc, P.; Jérôme, M.; Vincent, C.; Xavier, M.; Christine, G. J. Org. Chem., 2015, 80, 595.
17. [17]
  Zeba, N. S.; Kulsum, K. ACS Sustainable Chem. Eng. 2014, 2, 1187.
18. [18]
  Wang, R.; Liu, Z. Q. J. Org. Chem. 2012, 77, 3952.
19. [19]
  Marcos, A. P. M.; Clarissa, P. F.; Dayse, N. M.; Lilian, B.; Pablo, M. Chem. Rev. 2009, 109, 4140.
20. [20]
  Maneeporn, P.; Romain, R.; Miho, H.; Waraporn, P.; Vudhichai, P.; Keiji, M. J. Org. Chem. 2015, 80, 6959.
21. [21]
  Haline, G. O. A.; Tatiani, B. L.; Aline, L. O.; Heibbe C. B. Oliveira.; Fabricio, M. S.; Fabio, C. G.; Roberto, Y. S.; Wender, A. Silva.; Brenno, A. D. N. J. Org. Chem. 2014, 79, 3383.
22. [22]
23. [23]
1. [1]
  Yujing Chen , Hongqun Ouyang , Dan Zhao , Yanyan Chu , Zhengping Qiao . Recommendations for the Content and Instruction of the Physical Chemistry Experiment “Construction of Ternary Liquid-Liquid Phase Diagrams”. University Chemistry, 2025, 40(7): 359-366. doi: 10.12461/PKU.DXHX202409120
2. [2]
  Bing LIU , Huang ZHANG , Hongliang HAN , Changwen HU , Yinglei ZHANG . Visible light degradation of methylene blue from water by triangle Au@TiO₂ mesoporous catalyst. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 941-952. doi: 10.11862/CJIC.20230398
3. [3]
  Lina Guo , Ruizhe Li , Chuang Sun , Xiaoli Luo , Yiqiu Shi , Hong Yuan , Shuxin Ouyang , Tierui Zhang . 层状双金属氢氧化物的层间阴离子对衍生的Ni-Al₂O₃催化剂光热催化CO₂甲烷化反应的影响. Acta Physico-Chimica Sinica, 2025, 41(1): 2309002-. doi: 10.3866/PKU.WHXB202309002
4. [4]
  Wenlong LI , Xinyu JIA , Jie LING , Mengdan MA , Anning ZHOU . Photothermal catalytic CO₂ hydrogenation over a Mg-doped In₂O_3-x catalyst. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 919-929. doi: 10.11862/CJIC.20230421
5. [5]
  Kun WANG , Wenrui LIU , Peng JIANG , Yuhang SONG , Lihua CHEN , Zhao DENG . Hierarchical hollow structured BiOBr-Pt catalysts for photocatalytic CO₂ reduction. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1270-1278. doi: 10.11862/CJIC.20240037
6. [6]
  Haodong JIN , Qingqing LIU , Chaoyang SHI , Danyang WEI , Jie YU , Xuhui XU , Mingli XU . NiCu/ZnO heterostructure photothermal electrocatalyst for efficient hydrogen evolution reaction. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1068-1082. doi: 10.11862/CJIC.20250048
7. [7]
  Juntao Yan , Liang Wei . 2D S-Scheme Heterojunction Photocatalyst. Acta Physico-Chimica Sinica, 2024, 40(10): 2312024-. doi: 10.3866/PKU.WHXB202312024
8. [8]
  Yang WANG , Xiaoqin ZHENG , Yang LIU , Kai ZHANG , Jiahui KOU , Linbing SUN . Mn single-atom catalysts based on confined space: Fabrication and the electrocatalytic oxygen evolution reaction performance. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2175-2185. doi: 10.11862/CJIC.20240165
9. [9]
  Zhanggui DUAN , Yi PEI , Shanshan ZHENG , Zhaoyang WANG , Yongguang WANG , Junjie WANG , Yang HU , Chunxin LÜ , Wei ZHONG . Preparation of UiO-66-NH₂ supported copper catalyst and its catalytic activity on alcohol oxidation. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 496-506. doi: 10.11862/CJIC.20230317
10. [10]
  Zhiquan Zhang , Baker Rhimi , Zheyang Liu , Min Zhou , Guowei Deng , Wei Wei , Liang Mao , Huaming Li , Zhifeng Jiang . Insights into the Development of Copper-based Photocatalysts for CO₂ Conversion. Acta Physico-Chimica Sinica, 2024, 40(12): 2406029-. doi: 10.3866/PKU.WHXB202406029
11. [11]
  Wen YANG , Didi WANG , Ziyi HUANG , Yaping ZHOU , Yanyan FENG . La promoted hydrotalcite derived Ni-based catalysts: In situ preparation and CO₂ methanation performance. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 561-570. doi: 10.11862/CJIC.20230276
12. [12]
  Yulian Hu , Xin Zhou , Xiaojun Han . A Virtual Simulation Experiment on the Design and Property Analysis of CO₂ Reduction Photocatalyst. University Chemistry, 2025, 40(3): 30-35. doi: 10.12461/PKU.DXHX202403088
13. [13]
  Peng YUE , Liyao SHI , Jinglei CUI , Huirong ZHANG , Yanxia GUO . Effects of Ce and Mn promoters on the selective oxidation of ammonia over V₂O₅/TiO₂ catalyst. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 293-307. doi: 10.11862/CJIC.20240210
14. [14]
  Hailang JIA , Hongcheng LI , Pengcheng JI , Yang TENG , Mingyun GUAN . Preparation and performance of N-doped carbon nanotubes composite Co₃O₄ as oxygen reduction reaction electrocatalysts. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 693-700. doi: 10.11862/CJIC.20230402
15. [15]
  Jingzhao Cheng , Shiyu Gao , Bei Cheng , Kai Yang , Wang Wang , Shaowen Cao . 4-氨基-1H-咪唑-5-甲腈修饰供体-受体型氮化碳光催化剂的构建及其高效光催化产氢研究. Acta Physico-Chimica Sinica, 2024, 40(11): 2406026-. doi: 10.3866/PKU.WHXB202406026
16. [16]
  Yufang GAO , Nan HOU , Yaning LIANG , Ning LI , Yanting ZHANG , Zelong LI , Xiaofeng LI . Nano-thin layer MCM-22 zeolite: Synthesis and catalytic properties of trimethylbenzene isomerization reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1079-1087. doi: 10.11862/CJIC.20240036
17. [17]
  Bing WEI , Jianfan ZHANG , Zhe CHEN . Research progress in fine tuning of bimetallic nanocatalysts for electrocatalytic carbon dioxide reduction. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 425-439. doi: 10.11862/CJIC.20240201
18. [18]
  Xiaofang Li , Zhigang Wang . Modulating d_z²-orbital occupancy of Au cocatalysts for enhanced photocatalytic H₂O₂ production. Acta Physico-Chimica Sinica, 2025, 41(7): 100080-. doi: 10.1016/j.actphy.2025.100080
19. [19]
  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
20. [20]
  Yi YANG , Shuang WANG , Wendan WANG , Limiao CHEN . Photocatalytic CO₂ reduction performance of Z-scheme Ag-Cu₂O/BiVO₄ photocatalyst. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 895-906. doi: 10.11862/CJIC.20230434

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(885)
HTML views(73)

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