Citation: Wang Min, Pan He, Jiang Hongxu, Zhang Shun. One-Pot Synthesis of N1-Substituted 3, 4-Dihydropyrimidin-2(1H)-ones Catalyzed by Stannous Chloride Dihydrate[J]. Chemistry, ;2017, 80(9): 863-867. shu

One-Pot Synthesis of N1-Substituted 3, 4-Dihydropyrimidin-2(1H)-ones Catalyzed by Stannous Chloride Dihydrate

College of Chemistry & Chemical Engineering, Bohai University, Jinzhou 121013

Received Date: 23 February 2017
Accepted Date: 11 May 2017

Figures(2)

N1-Substituted 3, 4-dihydropyrimidin-2(1H)-ones were synthesized by a SnCl₂ catalysed three components one-pot reaction using aromatic aldehydes, ethyl acetoacetate (methyl acetoacetate) and monosubstituted urea as raw materials under solvent-free conditions. Effects of the amount of catalyst and the reaction temperature on the yields of product were studied. The structures of the titled products were characterized by IR, ¹H NMR, ¹³C NMR and elemental analysis. A mechanism to rationalize the reaction was proposed. This synthetic method has the advantages of short reaction time, mild reaction conditions, high yield, high catalytic activity, inexpensive catalyst and environmentally benign etc.
- 3, 4-Dihydropyrimidin-2(1H)-ones,
- Stannous chloride dihydrate,
- One pot synthesis,
- Solvent free
1. [1]
  H F Zhang, R F Schinazi, C K Chu. Bioorg. Med. Chem., 2006, 14(24):8314~8322.
2. [2]
  E D Clercq. J. Med. Chem., 1986, 29(9):1561~1569.
3. [3]
  S W Fewell, C M Smith, M A Lyon et al. J. Biol. Chem., 2004, 279(49):51131~51140.
4. [4]
  S N Mokale, S S Shinde, R D Elgire et al. Bioorg. Med. Chem. Lett., 2010, 20(15):4424~4426.
5. [5]
  K S Atwal, G C Rovnyak, S D Kimball et al. J. Med. Chem., 1990, 33(9):2629~2635.
6. [6]
  P Biginelli. Gazz. Chim. Ital., 1893, 23(3):360~413.
7. [7]
  K Singh, D Arora, E Poremsky et al. Eur. J. Med. Chem., 2009, 44(5):1997~2001.
8. [8]
  P Zalavadiya, S Tala, J Akbari et al. Arch. Pharm. Chem. Life Sci., 2009, 342(8):469~475.
9. [9]
  C O Kappe, D Kumar, R S Varma. Synthesis, 1999, (10):1799~1803.
10. [10]
  H Salehi, Q X Guo. Chin. J. Chem., 2005, 23(1):91~97.
11. [11]
  L Ismaili, A Nadaradjane, L Nicod et al. Eur. J. Med. Chem., 2008, 43(6):1270~1275.
12. [12]
  S Besoluk, M Kucukislamoglu, M Nebioglu et al. J. Iran. Chem. Soc., 2008, 5(1):62~66.
13. [13]
  G Aridoss, Y T Jeong. Bull. Kor. Chem. Soc., 2010, 31(4):863~868.
14. [14]
  W J Li, S Liu, P He et al. Tetrahedron, 2010, 66(41):8151~8159.
15. [15]
  Q F Cheng, Q F Wang, X Y Xu et al. J. Heterocycl. Chem., 2010, 47(3):624~628.
16. [16]
  H R Memarian, M Ranjbar. J. Chin. Chem. Soc., 2011, 58(4):522~527.
17. [17]
18. [18]
  S Putatunda, S Chakraborty, S Ghosh et al. Eur. J. Med. Chem., 2012, 54(8):223~231.
19. [19]
  C O Kappe. J. Org. Chem., 1997, 62(21):7201~7204.
1. [1]
  Renxiao Liang , Zhe Zhong , Zhangling Jin , Lijuan Shi , Yixia Jia . A Palladium/Chiral Phosphoric Acid Relay Catalysis for the One-Pot Three-Step Synthesis of Chiral Tetrahydroquinoline. University Chemistry, 2024, 39(5): 209-217. doi: 10.3866/PKU.DXHX202311024
2. [2]
  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
3. [3]
  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
4. [4]
  Yukun Chang , Haoqin Huang , Baolei Wang . Preparation of Trans-Cinnamic Acid via “One-Pot” Protocol of Aldol Condensation-Hydrolysis Reaction: Recommending an Improved Organic Synthesis Experiment. University Chemistry, 2024, 39(4): 322-328. doi: 10.3866/PKU.DXHX202309095
5. [5]
  Shuhui Li , Rongxiuyuan Huang , Yingming Pan . Electrochemical Synthesis of 2,5-Diphenyl-1,3,4-Oxadiazole: A Recommended Comprehensive Organic Chemistry Experiment. University Chemistry, 2025, 40(5): 357-365. doi: 10.12461/PKU.DXHX202407028
6. [6]
  Tianlong Zhang , Rongling Zhang , Hongsheng Tang , Yan Li , Hua Li . Online Monitoring and Mechanistic Analysis of 3,5-diamino-1,2,4-triazole (DAT) Synthesis via Raman Spectroscopy: A Recommendation for a Comprehensive Instrumental Analysis Experiment. University Chemistry, 2024, 39(6): 303-311. doi: 10.3866/PKU.DXHX202312006
7. [7]
  Yanglin Jiang , Mingqing Chen , Min Liang , Yige Yao , Yan Zhang , Peng Wang , Jianping Zhang . Experimental and Theoretical Investigations of Solvent Polarity Effect on ESIPT Mechanism in 4′-N,N-diethylamino-3-hydroxybenzoflavone. Acta Physico-Chimica Sinica, 2025, 41(2): 2309027-0. doi: 10.3866/PKU.WHXB202309027
8. [8]
  Nengmin ZHU , Wenhao ZHU , Xiaoyao YIN , Songzhi ZHENG , Hao LI , Zeyuan WANG , Wenhao WEI , Xuanheng CHEN , Weihai SUN . Preparation of high-performance CsPbBr₃ perovskite solar cells by the aqueous solution solvent method. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1131-1140. doi: 10.11862/CJIC.20240419
9. [9]
  Wen-Tao Ouyang , Jun Jiang , Yan-Fang Jiang , Ting Li , Yuan-Yuan Liu , Hong-Tao Ji , Li-Juan Ou , Wei-Min He . Sono-photocatalytic amination of quinoxalin-2(1H)-ones with aliphatic amines. Chinese Chemical Letters, 2024, 35(10): 110038-. doi: 10.1016/j.cclet.2024.110038
10. [10]
  Yanfen PENG , Xinyue WANG , Tianbao LIU , Xiaoshuo WU , Yujing WEI . Syntheses and luminescence of four Cd(Ⅱ)/Zn(Ⅱ) complexes constructed by 1,3‐bis(4H‐1,2,4‐triazole)benzene. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1416-1426. doi: 10.11862/CJIC.20250018
11. [11]
  Jingzhao Cheng , Shiyu Gao , Bei Cheng , Kai Yang , Wang Wang , Shaowen Cao . Construction of 4-Amino-1H-imidazole-5-carbonitrile Modified Carbon Nitride-Based Donor-Acceptor Photocatalyst for Efficient Photocatalytic Hydrogen Evolution. Acta Physico-Chimica Sinica, 2024, 40(11): 2406026-0. doi: 10.3866/PKU.WHXB202406026
12. [12]
  Gaofeng WANG , Shuwen SUN , Yanfei ZHAO , Lixin MENG , Bohui WEI . Structural diversity and luminescence properties of three zinc coordination polymers based on bis(4-(1H-imidazol-1-yl)phenyl)methanone. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 849-856. doi: 10.11862/CJIC.20230479
13. [13]
  Yu Xiong , Li-Jun Hu , Jian-Guo Song , Di Zhang , Yi-Shuang Peng , Xiao-Jun Huang , Jian Hong , Bin Zhu , Wen-Cai Ye , Ying Wang . Structure elucidation of plumerubradins A–C: Correlations between ¹H NMR signal patterns and structural information of [2+2]-type cyclobutane derivatives. Chinese Chemical Letters, 2025, 36(5): 110149-. doi: 10.1016/j.cclet.2024.110149
14. [14]
  Xiao-Ming Chen , Lianhui Song , Jun Pan , Fei Zeng , Yi Xie , Wei Wei , Dong Yi . Visible-light-induced four-component difunctionalization of alkenes to construct phosphorodithioate-containing quinoxalin-2(1H)-ones. Chinese Chemical Letters, 2024, 35(11): 110112-. doi: 10.1016/j.cclet.2024.110112
15. [15]
  Qiang Feng , Jindong Hao , Ya Hu , Rong Fu , Wei Wei , Dong Yi . Photocatalytic multi-component synthesis of ester-containing quinoxalin-2(1H)-ones using water as the hydrogen donor. Chinese Chemical Letters, 2025, 36(6): 110582-. doi: 10.1016/j.cclet.2024.110582
16. [16]
  Zhuoming Liang , Ming Chen , Zhiwen Zheng , Kai Chen . Multidimensional Studies on Ketone-Enol Tautomerism of 1,3-Diketones By ¹H NMR. University Chemistry, 2024, 39(7): 361-367. doi: 10.3866/PKU.DXHX202311029
17. [17]
  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
18. [18]
  Runze Liu , Yankai Bian , Weili Dai . Qualitative and quantitative analysis of Brønsted and Lewis acid sites in zeolites: A combined probe-assisted 1H MAS NMR and NH3-TPD investigation. Chinese Journal of Structural Chemistry, 2024, 43(4): 100250-100250. doi: 10.1016/j.cjsc.2024.100250
19. [19]
  Jingjing QING , Fan HE , Zhihui LIU , Shuaipeng HOU , Ya LIU , Yifan JIANG , Mengting TAN , Lifang HE , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and anticancer activity of two complexes of dimethylglyoxime organotin. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1301-1308. doi: 10.11862/CJIC.20240003
20. [20]
  Xinhao Yan , Guoliang Hu , Ruixi Chen , Hongyu Liu , Qizhi Yao , Jiao Li , Lingling Li . Polyethylene Glycol-Ammonium Sulfate-Nitroso R Salt System for the Separation of Cobalt (II). University Chemistry, 2024, 39(6): 287-294. doi: 10.3866/PKU.DXHX202310073

Get Citation

PDF

XML

Metrics

PDF Downloads(3)
Abstract views(1226)
HTML views(104)

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