SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

2020 , Vol. 40 >Issue 9: 2988 - 2993

DOI: https://doi.org/10.6023/cjoc202003043

Synthesis of N-Substituted Decahydroacridine-1,8-diones Promoted by Deep Eutectic Solvents

  • Xiao Liwei ,
  • Liu Guangxian ,
  • Li Zheng ,
  • Ren Ping ,
  • Ren Lilei ,
  • Kong Jie
Expand
  • College of Chemistry and Material Science, Langfang Normal University, Langfang, Hebei 065000

Received date: 2020-03-16

  Revised date: 2020-05-22

  Online published: 2020-06-19

Supported by

Project supported by the Educational Commission of Hebei Province (Nos. ZD2020153, ZD2019036) and the Science and Technology Bureau of Langfang City (No. 2019011018).

Fold

Abstract

In the deep eutectic solvents (DES) consisted of choline chloride/zinc chloride(ChCl/ZnCl2), a series of N-substi-tuted decahydroacridine-1,8-diones and decahydroacridine-1,8-diones were synthesized from diketones, aromatic aldehydes, ammonium acetates or aromatic amines with 75%~92% yields at 80~90 ℃ in 1~2 h. The advantages of the method are wild reaction condition, simple operation, short reaction time, high yield and friendly to environment.

Key words： deep eutectic solvent; decahydroacridine-1,8-diones; multicomponent reaction; green chemistry

Cite this article

Xiao Liwei , Liu Guangxian , Li Zheng , Ren Ping , Ren Lilei , Kong Jie . Synthesis of N-Substituted Decahydroacridine-1,8-diones Promoted by Deep Eutectic Solvents[J]. Chinese Journal of Organic Chemistry, 2020 , 40(9) : 2988 -2993 . DOI: 10.6023/cjoc202003043

References

[1] Mallu, L.; Thirumalai, D.; Asharani, I. V. Chem. Biol. Drug. Des. 2017, 90, 520.
[2] Kaya, M.; Yıldırır, Y.; Çelik, G. Y. Med. Chem. Res. 2010, 20, 293.
[3] Kaya, M.; Yıldırır, Y.; Çelik, G. Y. Pharm. Chem. J. 2015, 48, 722.
[4] Alvala, M.; Bhatnagar, S.; Ravi, A.; Jeankumar, V. U.; Manjashetty, T. H.; Yogeeswari, P.; Sriram, D. Bioorg. Med. Chem. Lett. 2012, 22, 3256.
[5] Tu, S.; Miao, C.; Fang, F.; Youjian, F.; Li, T.; Zhuang, Q.; Zhang, X.; Zhu, S.; Shi, D. Bioorg. Med. Chem. Lett. 2004, 14, 1533.
[6] Esirden, I.; Ulus, R.; Aday, B.; Tanç, M.; Supuran, C. T.; Kaya, M. Bioorg. Med. Chem. 2015, 23, 6573.
[7] Velu, R.; Won, N.; Kwag, J.; Jung, S.; Hur, J.; Kim, S.; Park, N. New J. Chem. 2012, 36, 1725.
[8] Kaya, M.; Yıldırır, Y.; Türker, L. J. Heterocycl. Chem. 2009, 46, 294.
[9] Periyasami, G.; Rajesh, R.; Arumugam, N.; Raghunathan, R.; Ganesan, S.; Maruthamuthu, P. J. Mater. Chem. A 2013, 1, 14666.
[10] Ashokkumar, P.; Ramakrishnan, V. T.; Ramamurthy, P. J. Phys. Chem. B 2011, 115, 84.
[11] Xia, J.-J.; Zhang, K.-H. Molecules 2012, 17, 5339.
[12]]Jin, T.-S.; Zhang, J.-S.; Guo, T.-T.; Wang, A.-Q.; Li, T.-S. Synthesis 2004, 2001.
[13] Chandrasekhar, S.; Rao, Y. S.; Sreelakshmi, L.; Mahipal, B.; Reddy, C. R. Synthesis 2008, 1737.
[14] Kidwai, M.; Bhatnagar, D. Tetrahedron Lett. 2010, 51, 2700.
[15] Saeed, B.; Fatemeh, C.; Fateme, D.; Hamid Reza, B. Chin. J. Chem. 2009, 27, 1953.
[16] Vahdat, S. M.; Akbari, M. Orient. J. Chem. 2011, 27, 1573.
[17] Rad-Moghadam, K.; Azimi, S. C. J. Mol. Catal. A:Chem. 2012, 363, 465.
[18] Zhu, A.; Liu, R.; Du, C.; Li, L. RSC Adv. 2017, 7, 6679.
[19] Shi, D.; Ni, S.; Dou, G. Chin. J. Org. Chem. 2009, 29, 788(in Chinese). (史达清, 倪赛男, 窦国兰, 有机化学, 2009, 29, 788.)
[20] Safaei, H. R.; Safaei, M.; Shekouhy, M. RSC Adv. 2015, 5, 97.
[21] Das, B.; Thirupathi, P.; Mahender, I.; Reddy, V. S.; Rao, Y. K. J. Mol. Catal. A:Chem. 2006, 247, 233.
[22] Hong, M.; Xiao, G. J. Fluorine Chem. 2012, 144, 7.
[23] Kahandal, S. S.; Burange, A. S.; Kale, S. R.; Prinsen, P.; Luque, R.; Jayaram, R. V. Catal. Commun. 2017, 97, 138.
[24] Ramesh, K. B.; Pasha, M. A. Bioorg. Med. Chem. Lett. 2014 24, 3907.
[25] Aday, B.; Yıldız, Y.; Ulus, R.; Eris, S.; Sen, F.; Kaya, M. New J. Chem. 2016, 40, 748.
[26] Pamuka, H.; Adayb, B.; Şena, F.; Kaya, M. RSC Adv. 2015, 5, 49295.
[27] Zareia, Z.; Akhlaghinia, B. New J. Chem. 2017, 41, 15485.
[28] Rafiee, E.; Eavani, S.; Khodayari, M. Chin. J. Catal. 2013, 34, 1513.
[29] Khojastehnezhad, A.; Rahimizadeh, M.; Eshghi, H.; Moeinpour, F.; Bakavoli, M. Chin. J. Catal. 2014, 35, 376.
[30] Das, P.; Dutta, A.; Bhaumik, A.; Mukhopadhyay, C. Green Chem. 2014, 16, 1426.
[31] Mahesh, P.; Guruswamy, K.; Diwakar, B. S.; Devi, B. R.; Murthy, Y. L. N.; Kollu, P.; Pammi, S. V. N. Chem. Lett. 2015, 44, 1386.
[32] Nasr-Esfahani, M.; Elhamifar, D.; Amadeh, T.; Karimi, B. RSC Adv. 2015, 5, 13087.
[33] Singh, S. K.; Singh, K. N. J. Heterocycl. Chem. 2011, 48, 69.
[34] Tu, S.; Wang, Q.; Zhang, Y.; Xu, J.; Zhang, J.; Zhu, X.; Shi, F. J. Heterocycl. Chem. 2006 3, 1647.
[35] Chen, W.; Xue, Z.; Wang, J.; Jiang, J.; Zhao, X.; Mu, T. Acta Phys. Chim. Sin. 2018, 34, 904.
[36] Li, Y.; Gong, X.; Liu, L.; Dong, J. Chin. J. Chem. 2016, 34, 419.
[37] Xiong, X.; Han, Q.; Shi, L.; Xiao, S.; Bi, C. Chin. J. Org. Chem. 2016, 36, 480(in Chinese). (熊兴泉, 韩骞, 石霖, 肖上运, 毕成, 有机化学, 2016, 36, 480.)
[38] Hou, Y.; Yao, C.; Wu, W. Acta Phys. Chim. Sin. 2018, 34, 873.
[39] Liu, P.; Hao, J.-W.; Mo, L.-P.; Zhang, Z.-H. RSC Adv. 2015, 5, 48675.
[40] Zhang, M.; Liu, Y.-H.; Shang, Z.-R.; Hu, H.-C.; Zhang, Z.-H. Catal. Commun. 2017, 88, 39.
[41] Zhang, M.; Liu, P.; Liu, Y.-H.; Shang, Z.-R.; Hu, H.-C.; Zhang, Z.-H. RSC Adv. 2016, 6, 106160.
[42] Ma, C.-T.; Liu, P.; Wu, W.; Zhang, Z.-H. J. Mol. Liq. 2017, 242, 606.
[43] Gao, G.; Wang, P.; Liu, P.; Zhang, W.; Mo, L.; Zhang, Z. Chin. J. Org. Chem. 2018, 38, 846(in Chinese). (高歌, 王萍, 刘鹏, 张卫红, 默丽萍, 张占辉, 有机化学, 2018, 38, 846.)
[44] Navarro, C. A.; Sierra, C. A.; Ochoa-Puentes, C. RSC Adv. 2016, 6, 65355.
[45] Zhang, W.-H.; Chen, M.-N.; Hao, Y.; Jiang, X.; Zhou, X.-L.; Zhang, Z.-H. J. Mol. Liq. 2019, 278, 124.
Options
Outlines

/

〈 〉