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以二氯甲烷作为C1合成子一锅法连续合成不对称二芳基甲烷。

One-pot sequential synthesis of unsymmetrical diarylmethanes using methylene chloride as a C1-synthon.

作者信息

Cui Xueli, Chen Chunming, Xie Mei, Zhao Taotao, Yi Jianfeng, Sun Weiqiang, Xiong Zhuang, Hu Jinhui, Wong Wing-Leung, Wu Jia-Qiang

机构信息

School of Pharmacy and Food Engineering, Wuyi University, No. 99 Yingbin Road, Jiangmen 529020, China.

State Key Laboratory of Chemical Biology and Drug Discovery, Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hung Hom, Kowloon, Hong Kong, China.

出版信息

Org Biomol Chem. 2024 Oct 9;22(39):7965-7970. doi: 10.1039/d4ob01158a.

Abstract

Bisindolylmethane (BIM) and its derivatives are widely used in the pharmaceutical industry due to their significant biological activities. However, most reported synthetic methods are focused on the synthesis of symmetric BIMs, while the synthesis of unsymmetrical BIMs remains a challenge. Herein, an unprecedented two-step one-pot method to afford unsymmetrically substituted 3,3'-BIM frameworks, using methylene chloride (DCM) as the C1-synthon is reported. In this protocol, the formation of two C-C bonds can be achieved a one-pot reaction. The utility of commercially available phenols and anilines was also demonstrated in the construction of unsymmetrical diarylmethanes. This protocol provides a straightforward approach to access diverse unsymmetrical diarylmethane derivatives under simple and mild conditions. The broad substrate compatibility and good functional group tolerance of the protocol support its practical application potential.

摘要

双吲哚甲烷(BIM)及其衍生物因其显著的生物活性而在制药工业中广泛应用。然而,大多数已报道的合成方法都集中在对称BIM的合成上,而不对称BIM的合成仍然是一个挑战。在此,报道了一种前所未有的两步一锅法,以二氯甲烷(DCM)作为C1合成子来制备不对称取代的3,3'-BIM骨架。在该方案中,两个C-C键的形成可以通过一锅反应实现。市售酚类和苯胺类化合物在不对称二芳基甲烷的构建中也得到了应用。该方案提供了一种在简单温和条件下获取多种不对称二芳基甲烷衍生物的直接方法。该方案广泛的底物兼容性和良好的官能团耐受性支持了其实际应用潜力。

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