Chinese Journal of Organic Chemistry >
An Efficient and Rapid Synthesis of 1H-Pyrazolo[3,4-d]-pyrimidin-4(5H)-one in Water
Received date: 2021-04-19
Revised date: 2021-05-10
Online published: 2021-06-08
Supported by
Chinese Academy of Medical Sciences Innovation Fund for Medical Sciences(2018-I2M-1-004); Non-profit Central Research Institute Fund of National Research Institute for Family Planing(2021GJZ05)
Abstract Pyrazolopyrimidinone compounds have many biological activities and been widely used due to the similar structure of purines in organisms. However, the traditional synthetic methods suffered from several drawbacks, such as acylation and cyclization. Herein, one pot cyclization of 1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one was developed by one pot conversion of 5-amino-4-cyano-pyrazole and aromatic aldehydes in the presence of sodium hydroxide using water as media. The reaction was carried out under the conditions of easily available raw materials, simple operation, and showed good tolerance to various functional groups.
Ziqi Su , Qi Zhang , Jieqiang Zhao , Tao Zhao , Wenyi Liu , Huiping Wang , Juan Xu , Jiarong Li . An Efficient and Rapid Synthesis of 1H-Pyrazolo[3,4-d]-pyrimidin-4(5H)-one in Water[J]. Chinese Journal of Organic Chemistry, 2021 , 41(9) : 3701 -3709 . DOI: 10.6023/cjoc202104043
| [1] | (a) Boolell, M.; Gepi-Attee, S.; Gingell, J. C.; Allen, M. J. Br. J. Urol. 1996, 78, 257. |
| [1] | (b) Terrett, N. K.; Bell, A. S.; Brown, D.; Ellis, P. Bioorg. Med. Chem. Lett. 1996, 6, 1819. |
| [1] | (c) Goldstein, I.; Lue, T. F.; Padma-Nathan, H.; Rosen, R. C.; Steers, W. D.; Wicker, P. A. N. Engl. J. Med. 1998, 338, 1397. |
| [2] | (a) Yü, T. F.; Gutman, A. B. Am. J. Med. 1964, 37, 885. |
| [2] | (b) Scott, J. T.; Hall, A. P.; Grahame, R. J. Occup. Environ. Med. 1966, 2, 321. |
| [2] | (c) Pacher, P.; Nivorozhkin, A.; Szabo, C. Pharmacol. Rev. 2006, 58, 87. |
| [3] | Yang, X. H.; Cao, X. B.; Jin, X. H.; Wu, M. H. Chin. J. Org. Chem. 2013, 33, 2080. (in Chinese). |
| [3] | ( 杨绪红, 曹晓蓓, 金小红, 吴鸣虎, 有机化学, 2013, 33, 2080.) |
| [4] | Yewale, S. B.; Ganorkar, S. B.; Baheti, K. G.; Shelke, R. U. Bioorg. Med. Chem. Lett. 2012, 22, 6616. |
| [5] | Ali, A.; Taylor, G. E.; Ellsworth, K.; Harris, G.; Painter. R.; Silver, L. L.; Young, K. J. Med. Chem. 2003, 46, 1824. |
| [6] | El-Sayed, W. A.; Ramiz, M. M. M.; Abdel-Rahman, A. H. Z. Naturforsch. C 2009, 64, 323. |
| [7] | Khobragade, C. N.; Bodade, R. G.; Konda, S. G.; Dawane, B. S.; Manwar, A. V. ChemInform 2010, 45, 1635. |
| [8] | El-Mekabaty, A. Chem. Heterocycl. Compd. 2015, 50, 1698. |
| [9] | Liu, H.; Wang, H. Q.; Liu, Z. J. Bioorg. Med. Chem. Lett. 2007, 17, 2203. |
| [10] | Rahmouni, A.; Romdhane, A.; Besbes, M.; Elie, N.; Jannet, H. B. Mediterr. J. Chem. 2014, 2, 679. |
| [11] | Kadry, H. H. Med. Chem. Res. 2014, 23, 5269. |
| [12] | Trivedi, A. R.; Dholariya, B. H.; Vakhariya, C. P.; Dodiya, D. K.; Ram, H. K.; Kataria, V. B.; Siddiqui, A. B.; Shah, V. H. Med. Chem. Res. 2012, 21, 1887. |
| [13] | Baviskar, A. T.; Banerjee, U. C.; Gupta, M.; Singh, R.; Kumar, S.; Gupta, M. K.; Kumar, S.; Raut, S. K.; Khullar, M.; Singh, S.; Kumar, R. Bioorg. Med. Chem. 2013, 21, 5782. |
| [14] | (a) Rashad, A. E.; Gaballa, S. T.; Hashem, A. I.; Osman, D. A. A.; Ali, M. M.; Hamed, S. F.; Abdel-Megeid, F. M. E. Pharma Chem. 2014, 6, 88. |
| [14] | (b) Hoon, G. H.; Jin, Y.; Raveendra, J.; Chang, H. O. Synth. Commun. 2018, 48, 1678. |
| [15] | Rahmouni, A.; Souiei, S.; Belkacem, M. A.; Romdhane, A.; Bouajila, J.; Jannet, H. B. Bioorg. Chem. 2016, 66, 160. |
| [16] | (a) Markwalder, J. A.; Arnone, M. R.; Benfield, P. A.; Boisclair, M.; Burton, C. R.; Chang, C. H.; Cox, S. S.; Czerniak, P. M.; Dean, C. L.; Doleniak, D.; Grafstrom, R.; Harrison, B. A.; Kaltenbach, III, R. F.; Nugiel, D. A.; Rossi, K. A.; Sherk, S. R.; Sisk, L. M.; Stouten, P.; Trainor, G. L.; Warland, P.; Seitz, S. P. J. Med. Chem. 2004, 47, 5894. |
| [16] | (b) Heo, Y. J.; Jeon, M. K. Tetrahedron 2017, 73, 5959. |
| [17] | (a) Rashad, A. E.; Hegab, M. I.; Abdel-Megeid, R. E.; Fathalla, N.; Abdel-Megeid, F. M. E. Eur. J. Med. Chem. 2009, 44, 3285. |
| [17] | (b) Rahmouni, A.; Romdhane, A.; Ben-said, A.; Guerinea, V.; Touboul, D.; Janne, H. B. Arabian J. Chem. 2014, 44, 1974. |
| [18] | (a) Singh, G. S.; Botlhole, L.; Mokgweetsi, P. Curr. Green Chem. 2016, 3, 318. |
| [18] | (b) Yue, H. L.; Bao, P. L.; Wang, L. L.; Lü, X. X.; Yang, D. S.; Wang, H.; Wei, W. Chin. J. Org. Chem. 2019, 39, 463. (in Chinese). |
| [18] | ( 岳会兰, 鲍鹏丽, 王雷雷, 吕晓霞, 杨道山, 王桦, 魏伟, 有机化学, 2019, 39, 463.) |
| [18] | (c) Chen, D.; Liu, J. C.; Zhang, X. Y.; Jiang, H. Z.; Li, J. H. Chin. J. Org. Chem. 2019, 39, 3353. (in Chinese). |
| [18] | ( 陈丹, 刘剑沉, 张馨元, 蒋合众, 李加洪, 有机化学, 2019, 39, 3353.) |
| [18] | (d) Lin, M.; Wu, F.; Liu, T. H.; Chen, Z. T.; Xu, X. Z.; Ke, F. Chin. J. Org. Chem. 2020, 40, 2563. (in Chinese). |
| [18] | ( 林媚, 吴凡, 刘天惠, 陈志涛, 许秀枝, 柯方, 有机化学, 2020, 40, 2563.) |
| [18] | (e) Xie, L. Y.; Peng, S.; Tan, J. X.; Sun, R. X.; Yu, X. Y.; Dai, N. N.; Tang, Z. L.; Xu, X. H.; He, W. M. ACS Sustainable Chem. Eng. 2018, 6, 16976. |
| [18] | (f) Peng, S.; Song, Y. X.; He, J. Y.; Tang, S. S.; Tan, J. X.; Cao, Z.; Lin, Y. W.; He, W. M. Chin. Chem. Lett. 2019, 30, 2287. |
| [18] | (g) Sun, K.; Lv, Q. Y.; Chen, X. L.; Qu, L. B.; Yu, B. Green Chem. 2021, 23, 232. |
| [19] | (a) Li, J. R.; Zhang, L. J.; Shi, D. X.; Li, Q.; Wang, D.; Wang, C. X.; Zhang, Q.; Zhang, L.; Fan, Y. Q. Synlett 2008, 39, 233. |
| [19] | (b) Yang, L. P.; Shi, D. X.; Chen, S.; Chai, H. X.; Huang, D. F.; Zhang, Q.; Li, J. R. Green Chem. 2012, 14, 945. |
| [20] | Robins, R. K. J. Am. Chem. Soc. 1956, 78, 784. |
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