Citation: Meng Zhiying, Gu Mengmeng, Wang Mengyao, Xu Jing, Gao Xu, Hao Ganlu, Rong Liangce. An Efficient Synthesis of New Azomethine Ylide: 1-(Diaminomethyl-eneammonio)(aryl) methyl-4, 4-dimethyl-2, 6-dioxocyclohexan-1-ide under Solvent-Free Conditions[J]. Chinese Journal of Organic Chemistry, ;2017, 37(1): 213-217. doi: 10.6023/cjoc201606021 shu

An Efficient Synthesis of New Azomethine Ylide: 1-(Diaminomethyl-eneammonio)(aryl) methyl-4, 4-dimethyl-2, 6-dioxocyclohexan-1-ide under Solvent-Free Conditions

School of Chemistry and Chemical Engineering, Jiangsu Normal University, Xuzhou 221116

Corresponding author: Rong Liangce, lcrong@jsnu.edu.cn
Received Date: 13 June 2016
Revised Date: 10 August 2016

Fund Project: the Natural Science Foundation of Jiangsu Normal University HXKY2015B001

Figures(3)

The zwitterionic compounds 1-(diaminomethyleneammonio)(aryl) methyl-4, 4-dimethyl-2, 6-dioxocyclohexan-1-ides were synthesized from the reaction of dimedone, aromatic aldehydes and guanidine carbonate catalyzed by NaOH under solvent-free conditions.This is the new type azomethine ylide compound that has not been reported previously.The other advantages of this reaction were simple operation, short reaction time, and environmental friendly.The products were identified by ¹H NMR, ¹³C NMR, IR and HRMS, and that of 4a was additionally confirmed by X-ray diffraction analysis.This reported approach is an effective way for the synthesis of azomethine ylide.
- dimedone,
- guanidine carbonate,
- azomethine ylide,
- green synthesis
1. [1]
  Wittig, G.; Rieber, M. Liebigs Ann. Chem. 1949, 562, 187. doi: 10.1002/(ISSN)1099-0690
2. [2]
  Varga, L. T.; Nagy, G.; Dormän, F.; Kälmän, L.; Ürge, F.; Davas, F. J. Comb. Chem. 2006, 8, 338. doi: 10.1021/cc0501514
3. [3]
  Wang, Q. F.; Hui, L.; Hou, H.; Yan, C. G. J. Comb. Chem. 2010, 12, 260. doi: 10.1021/cc900161z
4. [4]
  Jursic, B. S.; Neumann, D. M.; Moore, Z.; Stevens, E. D. J. Org. Chem. 2002, 67, 2372. doi: 10.1021/jo0161431
5. [5]
  Sosnovskikh, V. Y.; Usachev, B. I.; Sizov, A. Y.; Vorontsov, I. I.; Shklyaev, Y. V. Org. Lett. 2003, 5, 3123. doi: 10.1021/ol0351448
6. [6]
  Shaabani, A.; Rezayan, A. H.; Sarvary, A.; Heidary, M.; Ng, S. W. Tetrahedron 2009, 65, 6063. doi: 10.1016/j.tet.2009.05.055
7. [7]
  Liu, W.-J.; Chen, X.-H.; Gong, L.-Z. Org. Lett. 2008, 10, 5357. doi: 10.1021/ol802177s
8. [8]
  Li, X. F.; Yi, R. O.; Liu, B.; Li, Z. K.; Yu, X. Y.; Yi, P. G. Chin. J. Org. Chem. 2012, 32, 2309(in Chinese). doi: 10.6023/cjoc201207027
9. [9]
  Wang, F.; Bai, D. L. Chin. J. Org. Chem. 2006, 26, 9(in Chinese).
10. [10]
  Zhang, Z.; Zha, Z.; Gan, C.; Pan, C.; Zhou, Y.; Wang, Z.; Zhou, M. M. J. Org. Chem. 2006, 71, 4339. doi: 10.1021/jo060372b
11. [11]
  Shen, Y.; Atobe, M.; Fuchigami, T. Org. Lett. 2004, 6, 2441. doi: 10.1021/ol049152f
12. [12]
  Dalvi, P. B.; Lin, S. F.; Paike, V.; Sun, C. M. ACS Comb. Sci. 2015, 17, 421. doi: 10.1021/acscombsci.5b00053
13. [13]
  Wang, J. J.; Feng, X.; Xun, Z.; Shi, D. Q.; Huang, Z. B. J. Org. Chem. 2015, 80, 8435. doi: 10.1021/acs.joc.5b01314
14. [14]
  Huang, Y. B.; Yang, T.; Liu, A. F.; Zhou, X. H.; Pan, H. J. Org. Chem. 2016, 36, 1438(in Chinese).
15. [15]
  Zhang, D.; Cheng, T.; Zhao, Q.; Xu, J.; Liu, G. Org. Lett. 2014, 16, 5764. doi: 10.1021/ol502832a
16. [16]
  Hou, Y.; Lu, S.; Liu, G. J. Org. Chem. 2013, 78, 8386. doi: 10.1021/jo401077q
17. [17]
  Yan, H. H.; Zhao, B. L.; Gao, Y.; Du, D. M. Chin. J. Org. Chem. 2016, 36, 1643(in Chinese). doi: 10.6023/cjoc201512021
18. [18]
  Koguchi, S.; Izawa, K.; ACS Comb. Sci. 2014, 16, 381. doi: 10.1021/co500065e
19. [19]
  Feng, X.; Wang, J. J.; Lin, W.; Zhang, J. J.; Huang, Z. B.; Shi, D. Q. Chin. J. Chem. 2014, 32, 889. doi: 10.1002/cjoc.201400312
20. [20]
  Sun, D. Z.; Jiang, G. F.; Xie, Z. B.; Le, Z. G. Chin. J. Chem. 2015, 33, 409. doi: 10.1002/cjoc.v33.4
21. [21]
  Salum, M. L.; Robles, C. J.; Erra-Balsells, R. Org. Lett. 2010, 12, 4808. doi: 10.1021/ol1019508
22. [22]
  Zhao, H. Y.; Yin, F. G.; Yu, L. Y.; Li, B. G.; Bian, Z. X. Chin. J. Org. Chem. 2016, 36, 1118(in Chinese). doi: 10.6023/cjoc201511045
23. [23]
  Sable, G. A.; Lim, D. J. Org. Chem. 2015, 80, 7486. doi: 10.1021/acs.joc.5b01055
24. [24]
  Chen, T.; Foo, T. J. Y.; Yeung, Y. Y. ACS Catal. 2015, 5, 4751. doi: 10.1021/acscatal.5b01182
25. [25]
  Jeganathan, I. M.; Pitchumani, K. ACS Sustainable Chem. Eng. 2014, 2, 1169. doi: 10.1021/sc400560v
26. [26]
  Azizi, N.; Aryanasab, F.; Saidi, M. R. Org. Lett. 2006, 8, 5275. doi: 10.1021/ol0620141
27. [27]
  Yusubov, M. S.; Wirth, T. Org. Lett. 2005, 7, 519. doi: 10.1021/ol047363e
28. [28]
  Lü, C. W.; Liu, Y. H.; Zhou, X. X. Chin. J. Org. Chem. 2016, 36, 1407(in Chinese). doi: 10.6023/cjoc201601010
1. [1]
  Tao Cao , Fang Fang , Nianguang Li , Yinan Zhang , Qichen Zhan . Green Synthesis of p-Hydroxybenzonitrile Catalyzed by Spinach Extracts under Red-Light Irradiation: Research and Exploration of Innovative Experiments for Pharmacy Undergraduates. University Chemistry, 2024, 39(5): 63-69. doi: 10.3866/PKU.DXHX202309098
2. [2]
  Chi Li , Jichao Wan , Qiyu Long , Hui Lv , Ying Xiong . N-Heterocyclic Carbene (NHC)-Catalyzed Amidation of Aldehydes with Nitroso Compounds. University Chemistry, 2024, 39(5): 388-395. doi: 10.3866/PKU.DXHX202312016
3. [3]
  Yurong Tang , Yunren Shi , Yi Xu , Bo Qin , Yanqin Xu , Yunfei Cai . Innovative Experiment and Course Transformation Practice of Visible-Light-Mediated Photocatalytic Synthesis of Isoquinolinone. University Chemistry, 2024, 39(5): 296-306. doi: 10.3866/PKU.DXHX202311087
4. [4]
  Feng Sha , Xinyan Wu , Ping Hu , Wenqing Zhang , Xiaoyang Luan , Yunfei Ma . Design of Course Ideology and Politics for the Comprehensive Organic Synthesis Experiment of Benzocaine. University Chemistry, 2024, 39(2): 110-115. doi: 10.3866/PKU.DXHX202307082
5. [5]
  Renxiu Zhang , Xin Zhao , Yunfei Zhang . Application of Electrochemical Synthesis in the Teaching of Organic Chemistry. University Chemistry, 2025, 40(4): 174-180. doi: 10.12461/PKU.DXHX202406116
6. [6]
  Jinyao Du , Xingchao Zang , Ningning Xu , Yongjun Liu , Weisi Guo . Electrochemical Thiocyanation of 4-Bromoethylbenzene. University Chemistry, 2024, 39(6): 312-317. doi: 10.3866/PKU.DXHX202310039
7. [7]
  Liangzhen Hu , Li Ni , Ziyi Liu , Xiaohui Zhang , Bo Qin , Yan Xiong . A Green Chemistry Experiment on Electrochemical Synthesis of Benzophenone. University Chemistry, 2024, 39(6): 350-356. doi: 10.3866/PKU.DXHX202312001
8. [8]
  Ping Song , Nan Zhang , Jie Wang , Rui Yan , Zhiqiang Wang , Yingxue Jin . Experimental Teaching Design on Synthesis and Antitumor Activity Study of Cu-Pyropheophorbide-a Methyl Ester. University Chemistry, 2024, 39(6): 278-286. doi: 10.3866/PKU.DXHX202310087
9. [9]
  Weikang Wang , Yadong Wu , Jianjun Zhang , Kai Meng , Jinhe Li , Lele Wang , Qinqin Liu . 三聚氰胺泡沫支撑的S型硫铟锌镉/硫掺杂氮化碳异质结的绿色H₂O₂合成：协同界面电荷转移调控与局域光热效应. Acta Physico-Chimica Sinica, 2025, 41(8): 100093-. doi: 10.1016/j.actphy.2025.100093
10. [10]
  Minna Ma , Yujin Ouyang , Yuan Wu , Mingwei Yuan , Lijuan Yang . Green Synthesis of Medical Chemiluminescence Reagents by Photocatalytic Oxidation. University Chemistry, 2024, 39(5): 134-143. doi: 10.3866/PKU.DXHX202310093
11. [11]
  Yinuo Wang , Siran Wang , Yilong Zhao , Dazhen Xu . Selective Synthesis of Diarylmethyl Anilines and Triarylmethanes via Multicomponent Reactions: Introduce a Comprehensive Experiment of Organic Chemistry. University Chemistry, 2024, 39(8): 324-330. doi: 10.3866/PKU.DXHX202401063
12. [12]
  Bingliang Li , Yuying Han , Dianyang Li , Dandan Liu , Wenbin Shang . One-Step Synthesis of Benorilate Guided by Green Chemistry Principles and in vivo Dynamic Evaluation. University Chemistry, 2024, 39(6): 342-349. doi: 10.3866/PKU.DXHX202311070
13. [13]
  Li'na ZHONG , Jingling CHEN , Qinghua ZHAO . Synthesis of multi-responsive carbon quantum dots from green carbon sources for detection of iron ions and L-ascorbic acid. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 709-718. doi: 10.11862/CJIC.20240280
14. [14]
  Yinwu Su , Xuanwen Zheng , Jianghui Du , Boda Li , Tao Wang , Zhiyan Huang . Green Synthesis of 1,3-Dibromoacetone Using Halogen Exchange Method: Recommending a Basic Organic Synthesis Teaching Experiment. University Chemistry, 2024, 39(5): 307-314. doi: 10.3866/PKU.DXHX202311092
15. [15]
  Yongqing Kuang , Jie Liu , Jianjun Feng , Wen Yang , Shuanglian Cai , Ling Shi . Experimental Design for the Two-Step Synthesis of Paracetamol from 4-Hydroxyacetophenone. University Chemistry, 2024, 39(8): 331-337. doi: 10.12461/PKU.DXHX202403012
16. [16]
  Yongpo Zhang , Xinfeng Li , Yafei Song , Mengyao Sun , Congcong Yin , Chunyan Gao , Jinzhong Zhao . Synthesis of Chlorine-Bridged Binuclear Cu(I) Complexes Based on Conjugation-Driven Cu(II) Oxidized Secondary Amines. University Chemistry, 2024, 39(5): 44-51. doi: 10.3866/PKU.DXHX202309092
17. [17]
  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
18. [18]
  Zhen Yao , Bing Lin , Youping Tian , Tao Li , Wenhui Zhang , Xiongwei Liu , Wude Yang . Visible-Light-Mediated One-Pot Synthesis of Secondary Amines and Mechanistic Exploration. University Chemistry, 2024, 39(5): 201-208. doi: 10.3866/PKU.DXHX202311033
19. [19]
  Junli Liu . Practice and Exploration of Research-Oriented Classroom Teaching in the Integration of Science and Education: a Case Study on the Synthesis of Sub-Nanometer Metal Oxide Materials and Their Application in Battery Energy Storage. University Chemistry, 2024, 39(10): 249-254. doi: 10.12461/PKU.DXHX202404023
20. [20]
  Changyan Sun , Hualei Zhou , Bin Dong . Application of “PBL” Teaching Mode in Inorganic Chemistry Experimental Education in the Perspective of Course Ideology and Politics: Taking Preparation of Manganese Carbonate as an Example. University Chemistry, 2024, 39(11): 378-383. doi: 10.12461/PKU.DXHX202402016

Get Citation

PDF

XML

Metrics

PDF Downloads(1)
Abstract views(1186)
HTML views(55)

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