Citation:
Chengbo Sun, Zhubao Zhang, Yizhong Chen, Yuhao Kuang, Xiaojian Liao, Pengju Feng. 一锅三步由硝基芳烃合成邻氨基酚衍生物[J]. University Chemistry,
;2022, 37(5): 211101.
doi:
10.3866/PKU.DXHX202111018
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硝基的选择性还原,羟胺的选择性保护,以及[3,3]-σ重排都是有机化学的基础内容。本实验将此三个基本反应融入于3.5 h的紧凑一锅法化学反应中,反应现象丰富且便于观察,利用薄层色谱能方便监测反应的进程。反应可以从简单的硝基芳烃一锅获取高官能化邻氨基酚衍生物,同时三步反应可以分解为三个单独的反应,且均能高收率得到相应化合物。产物可由硅胶柱层析纯化,化合物结构通过质谱、核磁共振波谱的解析进一步确定。该反应立足有机化学硝基官能团基础知识,适用于本科生学习官能团转化知识,观测多种实验现象,同时反应操作多样,用时紧凑,产率高,在邻氨基酚类衍生物制备中具有广泛的应用潜力。
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[1]
Knight, S. D.; Adams, N. D.; Burgess, J. L.; Chaudhari, A. M.; Darcy, M. G.; Donatelli, C. A.; Luengo, J. I.; Newlander, K. A.; Parrish, C. A.; Ridgers, L. H.; et al. ACS Med. Chem. Lett. 2010, 1, 39.
-
[2]
Benjahad, A.; Croisy, M.; Monneret, C.; Bisagni, E.; Mabire, D.; Coupa, S.; Poncelet, A.; Csoka, I.; Cuillemont, J.; Meyer, C.; et al. J. Med. Chem. 2005, 48, 1948.
-
[3]
Liu, Q.; Lu, Z.; Ren, W.; Shen, K.; Wang, Y.; Xu, Q. Chin. J. Chem. 2013, 31, 764.
-
[4]
(a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457. (b) Nigishi, A. Acc. Chem. Res. 1982, 15, 340.
-
[5]
Buchwald, S. L. Top Curr. Chem. 2002, 219, 131.
-
[6]
Lin, L.; Chem, X.; Zhao, J.; Lin, S.; Ma, G.; Liao, X.; Feng, P. Heterocycl. Commun. 2019, 25, 138.
-
[7]
Nakamura, I.; Jo, T.; Ishida, Y.; Tashiro, H.; Terada, M. Org. Lett. 2017, 19, 3059.
-
[8]
Liu, M.-C.; Lin, T.-S.; Sartorelli, A. C. J. Med. Chem. 1992, 35, 3672.
-
[9]
Wang, L.; Zhao, S.; Kong, X.; Cao, L.; Tian, S.; Ye, Y.; Qiao, C. Bioorg. Med. Chem. 2018, 26, 875.
-
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