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

doi:10.6023/cjoc201901050

有机化学 ›› 2019, Vol. 39 ›› Issue (7): 1945-1952.DOI: 10.6023/cjoc201901050 上一篇下一篇

研究论文

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

马会芳, 李文博, 阿布拉江·克依木

新疆大学化学化工学院石油天然气精细化工教育部&新疆维吾尔自治区重点实验室乌鲁木齐 830046

收稿日期:2019-01-29 修回日期:2019-03-07 发布日期:2019-04-09
通讯作者: 阿布拉江·克依木 E-mail:ablajan209@hotmail.com
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

Ma Huifang, Li Wenbo, Ablajan Keyume

Key Laboratory of Oil & Gas Fine Chemicals, Ministry of Education & Xinjiang Uyghur Autonomous Region, College of Chemistry and Chemical Engineering, Xinjiang University, Urumqi 830046

Received:2019-01-29 Revised:2019-03-07 Published:2019-04-09
Contact: 10.6023/cjoc201901050 E-mail:ablajan209@hotmail.com
Supported by:
Project supported by the National Science Foundation of China (No. 21462041).

文章分享

1. 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.PDF(16155KB)

摘要/Abstract

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

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.

Key words: dihydropyrimidine derivative, solid acidic ion exchange resin Amberlyst-15, one-pot reaction

引用此文

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.

Ma Huifang, Li Wenbo, Ablajan Keyume. 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[J]. Chin. J. Org. Chem., 2019, 39(7): 1945-1952.

导出引用 EndNote|Reference Manager|ProCite|BibTeX|RefWorks

分享此文

参考文献

[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.

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

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

PDF

补充材料

可视化

摘要/Abstract

引用此文

分享此文

参考文献

相关文章 3

编辑推荐

相关统计

本文评价

[1]	陈任宏, 吴桂贞, 杨凯, 叶斌, 陈庆凤, 汪朝阳. 一锅法合成N-呋喃酮基磺酰腙类化合物[J]. 有机化学, 2021, 41(7): 2750-2759.
[2]	胡智宇, 姜国芳, 祝志强, 龚伯桢, 谢宗波, 乐长高. 深共融溶剂促进的亨利-傅克烷基化串联反应[J]. 有机化学, 2021, 41(1): 325-332.
[3]	常青, 康娟, 张为钢, 王娟娟, 黄丹凤, 王克虎, 苏瀛鹏, 胡雨来. 锡粉促进下α-酰肼基-γ-戊烯酸乙酯的合成[J]. 有机化学, 2016, 36(12): 2920-2927.