Amberlyst-15催化下的二氢[1,2,4]三唑并[1,5-a]嘧啶类及二氢苯并[4,5]咪唑并[1,2-a]嘧啶类衍生物的一锅法合成
收稿日期: 2019-01-29
修回日期: 2019-03-07
网络出版日期: 2019-04-09
基金资助
国家自然科学基金（No.21462041）资助项目.
One-Pot Synthesis of Dihydro[1,2,4]triazolo[1,5-a]pyrimidines and Dihydrobenzo[4,5]imidazo[1,2-a]pyrimidine Derivatives Catalyzed by Amberlyst-15
Received date: 2019-01-29
Revised date: 2019-03-07
Online published: 2019-04-09
Supported by
Project supported by the National Science Foundation of China (No. 21462041).
在固体酸性离子交换树脂Amberlyst-15的催化作用下，以乙醇作为溶剂，以芳香醛、β-酮酸酯、3-氨基-1，2，4-三唑或者2-氨基苯并咪唑为原料经过三组分一锅法反应合成了一系列三唑并[1，5-a]嘧啶衍生物5a～5m及二氢苯并[4，5]咪唑并[1，2-a]嘧啶类衍生物6a～6g.该方法简单高效、具有反应时间短、后处理简单、底物适用范围较广以及催化剂可以循环利用4次催化活性无明显下降的优点，符合绿色化学的基本标准.
关键词： 二氢嘧啶衍生物; 固体酸性离子交换树脂Amberlyst-15; 一锅法反应
马会芳 , 李文博 , 阿布拉江·克依木 . Amberlyst-15催化下的二氢[1,2,4]三唑并[1,5-a]嘧啶类及二氢苯并[4,5]咪唑并[1,2-a]嘧啶类衍生物的一锅法合成[J]. 有机化学, 2019 , 39(7) : 1945 -1952 . DOI: 10.6023/cjoc201901050
Under the catalysis of solid acidic ion exchange resin Amberlyst-15, using ethanol as solvent, aromatic aldehyde, β-ketoester, and 3-amino-1,2,4-triazole or 2-aminobenzo as starting materials, a series of triazolo[1,5-a]pyrimidine derivatives 5a~5m and dihydrobenzo[4,5]imidazo[1,2-a]pyrimidines 6a~6g were synthesized by three-component one-pot reaction of imidazole derivatives. The method is simple and efficient, and has short reaction time, simple post-treatment and wide application range of the substrate. The catalyst can be recycled for 4 times without the significant decrease of catalytic activity. It conforms to the basic standard of green chemistry.
[1] Pandey, S. K.; Singh, A.; Singh, A. Eur. J. Med. Chem. 2009, 44, 1188.
[2] Kappe, C. O. Acc. Chem. Res. 2000, 33, 879.
[3] Martin, M. W.; Newcomb, J.; Nunes, J. J.; Boucher, C.; Chai, L.; Epstein, L. F.; Faust, T.; Flores, S.; Gallant, P. J. Med. Chem. 2008, 51, 1637.
[4] Magan, R.; Marin, C.; Rosales, M. J.; Salas, J. M.; Sanchez-Moreno, M. Pharmacology 2005, 73, 41.
[5] Pryadeina, M. V.; Burgart, Y. V.; Saloutin, V. I.; Kodess, M. I.; Ulomskii, E. N.; Rusinov, V. L. J. Org. Chem. 2004, 40, 902.
[6] Hu, M. F.; Liu, X. G.; Dong, F. S.; Xu, J.; Li, S. S.; Xu, H. Q.; Zheng, Y. Q. Food Chem. 2015, 175, 395.
[7] El Rady, E. A.; Barsy, M. A. J. Heterocycl. Chem. 2006, 43, 243.
[8] Insuasty, B.; Salcedo, A.; Quiroga, J.; Abonia, R.; Nogueras, M.; Cobo, J.; Salido, S. Heterocycl. Commun. 2004, 10, 399.
[9] (a) Lipson, V. V.; Desenko, S. M.; Shirobokova, M. G.; Borodina, V. V. Chem. Heterocycl. Compd. 2003, 39, 1213.
(b) Lipson, V. V.; Desenko, S. M.; Borodina, V. V.; Shirobokova, M. G.; Musatov, V. I. Russ. J. Org. Chem. 2005, 41, 114.
[10] (a) Yao, C. S.; Lei, S.; Wang, C. H.; Yu, C. X.; Tu, S. J. J. Heterocycl. Chem. 2008, 45, 1609.
(b). Shaabani, A.; Farhangi, E.; Rahmati, A. Comb. Chem. High Throughput Screen. 2006, 9, 771.
[11] (a) Shao, Q.; Li, Ch.; Cao, L.; Zhou, D.; Wang, Q.; Jiang, B.; Zhang, Y.; Hao, W. J. Heterocycl. Chem. 2008, 45, 411.
(b) Krishnamurthy, G.; Jagannath, K.V. J. Chem. Sci. 2013, 125, 807.
[12] Mousavi, M. R.; Maghsoodlou, M. T. Monatsh. Chem. 2004, 145, 1967.
[13] Chen, F. L.; Lei, M.; Hu, L. H. Tetrahedron 2013, 69, 2954.
[14] Puligoundla, R. G.; Karnakanti, S.; Bantu, R.; Kommu, N.; Kondra, S. B.; Nagarapu, L. Tetrahedron Lett. 2013, 54, 2480.
[15] Kumari, K.; Raghuvanshi, D. S.; Singh, K. N. Org. Prep. Proced. Int. 2012, 44, 460.
[16] Shaabani, A.; Farhangi, E.; Shaabani, S. Iran. J. Chem. Chem. Eng. 2013, 32, 3.
[17] Mousavi, M. R.; Maghsoodlou, M. T. J. Iran. Chem. Soc. 2015, 12, 743.
[18] Mousavi, M. R.; Maghsoodlou, M. T.; Hazeri, N.; HabibiKhorassani, S. M. J. Iran. Chem. Soc. 2015, 12, 1419.
[19] Heravi, M. M.; Derikvand, F.; Ranjbar, L. Synth. Commun. 2010, 40, 677.
[20] Seyyedi, N.; Shirini, F.; Langarudi, M. S. N.; Jashnani, S. J. Iran. Chem. Soc. 2017, 14, 1859.
[21] Cross, R. A.; Kalra, B. Science 2002, 297, 803.
[22] Das, B.; Damodar, K.; Chouwdhury, N.; Kumar, R. A. J. Mol. Catal. A: Chem. 2007, 274, 148.
[23] Bhanushali, M. J.; Nandurkar, N. S.; Bhor, M. D.; Bhanage, B. M. Catal. Commun. 2008, 9, 425.
[24] Qureshi, Z. S.; Deshmukh, K. M.; Tambade, P. J.; Bhanage, B. M. Tetrahedron Lett. 2010, 51, 724.
/
| 〈 |
|
〉 |
