- One-Pot Protocol to Synthesize 2-Aminophenols from Anilines via Palladium-Catalyzed C-H Acetoxylation
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This paper describes a facile one-pot protocol to synthesize 2-aminophenol derivatives via a palladium-catalyzed C-H acetoxylation strategy with 5-nitropyrimidine as a directing group (DG), which can be easily preinstalled and readily removed under mild condition after the coupling. In addition, the transformation is operationally simple, has high functional group tolerance, and is amenable to gram-scale. Moreover, several examples were shown that introduction/removal of 5-nitropyrimidine and the C-H oxylation sequence could be integrated in one pot.
- Zhao, Junhao,Huang, Yifeng,Ma, Guojian,Lin, Ling,Feng, Pengju
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p. 2084 - 2091
(2019/05/21)
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- Ortho-aminophenol derivative and preparation method thereof
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The invention first discloses a preparation method of an ortho-aminophenol derivative. The preparation method comprises the following steps: (1) by adopting an aryl amine compound as a substrate and 2-chloro-5-nitropyridine as a guiding base, reacting in acetonitrile, thus obtaining a pyridine aryl amine compound intermediate; (2) catalyzing the pyridine aryl amine compound intermediate in step (1) to make C-H activation reaction in a solvent by using iodobenzene diacetate as an oxidant and palladium acetate as a catalyst, thus obtaining an acetoxylation aniline derivative, draining, and thenperforming the chromatographic separation and purification; and (3) enabling the acetoxylation aniline derivative in step (2) to react in a tetrahydrofuran solvent for 30 min at a normal temperature by virtue of hydrazine hydrate, thus obtaining the ortho-aminophenol derivative, quenching, washing, extracting, drying, draining, and performing the chromatographic separation and purification. The invention also discloses the ortho-aminophenol derivative prepared by the method.
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Paragraph 0033; 0034; 0035
(2018/07/15)
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- Discovery of a series of 2,5-diaminopyrimidine covalent irreversible inhibitors of Bruton's tyrosine kinase with in vivo antitumor activity
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Bruton's tyrosine kinase (Btk) is an attractive drug target for treating several B-cell lineage cancers. Ibrutinib is a first-in-class covalent irreversible Btk inhibitor and has demonstrated impressive effects in multiple clinical trials. Herein, we present a series of novel 2,5-diaminopyrimidine covalent irreversible inhibitors of Btk. Compared with ibrutinib, these inhibitors exhibited a different selectivity profile for the analyzed kinases as well as a dual-action mode of inhibition of both Btk activation and catalytic activity, which counteracts a negative regulation loop for Btk. Two compounds from this series, 31 and 38, showed potent antiproliferative activities toward multiple B-cell lymphoma cell lines, including germinal center B-cell-like diffuse large B cell lymphoma (GCB-DLBCL) cells. In addition, compound 31 significantly prevented tumor growth in a mouse xenograft model.
- Li, Xitao,Zuo, Yingying,Tang, Guanghui,Wang, Yan,Zhou, Yiqing,Wang, Xueying,Guo, Tianlin,Xia, Mengying,Ding, Ning,Pan, Zhengying
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p. 5112 - 5128
(2014/07/08)
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