- Selective Carbon-Carbon Bond Amination with Redox-Active Aminating Reagents: A Direct Approach to Anilines?
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Amines are among the most fundamental motifs in chemical synthesis, and the introduction of amine building blocks via selective C—C bond cleavage allows the construction of nitrogen compounds from simple hydrocarbons through direct skeleton modification. Herein, we report a novel method for the preparation of anilines from alkylarenes via Schmidt-type rearrangement using redox-active amination reagents, which are easily prepared from hydroxylamine. Primary amines and secondary amines were prepared from corresponding alkylarenes or benzyl alcohols under mild conditions. Good compatibility and valuable applications of the transformation were also displayed.
- Qiu, Xu,Wang, Yachong,Su, Lingyu,Jin, Rui,Song, Song,Qin, Qixue,Li, Junhua,Zong, Baoning,Jiao, Ning
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supporting information
p. 3011 - 3016
(2021/09/13)
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- Design, synthesis, and in vitro/vivo anticancer activity of 4-substituted 7-(3-fluoro-4-methoxybenzyl)-7H-pyrrolo[2,3-d]pyrimidines
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In this paper, we report the design and synthesis of 4-substituted 7-(3-fluoro-4-methoxybenzyl)-7H-pyrrolo[2,3-d]pyrimidines of scaffold 6 as anticancer agents. A total of 19 derivatives of scaffold 6 bearing a C-4 alkoxy, dialkylamino, alkyl, vinyl, or phenyl substituent were synthesized and evaluated. Among them, compound 6q having a C-4 ethyl group and a benzylic methyl group showed the most potent in vitro anticancer activity, inhibiting the proliferation of Hela, MDA-MB-231, and MDA-MB-426 cancer cells at submicromolar concentrations (GI50: 0.11–0.58 μM). Compound 6q arrested the cell cycle of MDA-MB-231 at G2/M phase, and showed in vivo activity on nude mice bearing MDA-MB-231 xenografts. Compound 6q has served as an anticancer lead for further optimization.
- Tsai, Pei-Yi,Hu, Gong-Siang,Huang, Po-Hsun,Jheng, Huei-Lin,Lan, Chi-Hsuan,Chen, You-Sin,Chang, Jia-Ming,Chuang, Shih-Hsien,Huang, Jiann-Jyh
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p. 1761 - 1770
(2021/05/05)
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- Enantioselective installation of adjacent tertiary benzylic stereocentres using lithiation-borylation-protodeboronation methodology. Application to the synthesis of bifluranol and fluorohexestrol
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1,2-Diaryl ethanes bearing 1,2-stereogenic centres show interesting biological activity but their stereocontrolled synthesis has not been reported forcing a reliance of methods involving diastereomer and enantiomer separation. We have found that this clas
- Roesner, Stefan,Blair, Daniel J.,Aggarwal, Varinder K.
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p. 3718 - 3723
(2015/06/25)
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