Synthesis of diarylmethyl thioethers via a DABCO-catalyzed 1,6-conjugate addition reaction of p-quinone methides with organosulfur reagents. 2023

Ming-Shan Shuai, and Xiang Guan, and Xing-Hai Fei, and Mao Zhang, and Xiao-Zhong Fu, and Bin He, and Yong-Long Zhao
State Key Laboratory of Functions and Applications of Medicinal Plants, School of Pharmacy, and Engineering Research Center for the Development and Application of Ethnic Medicine and TCM (Ministry of Education), Guizhou Medical University Guiyang 550004 People's Republic of China zhaoyl05@126.com.

A rapid and simple method was developed for the synthesis of diarylmethyl thioethers via a DABCO-catalyzed 1,6-conjugate addition reaction of para-quinone methides (p-QMs) with organosulfur reagents. A series of diarylmethyl thioethers were synthesized at 13-85% yields by this method. After that, the antibacterial activities of synthesized diarylmethyl thioethers and their derivatives were evaluated. The MIC range (μg mL-1) against Staphylococcus aureus ATCC 25923 and clinically isolated methicillin-resistant S. aureus was 8-128 and 64-128, respectively.

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