Light-assisted green and efficient construction of thiadiazole/selenadiazole derivatives†

IF 9.3 1区 化学 Q1 CHEMISTRY, MULTIDISCIPLINARY Green Chemistry Pub Date : 2024-07-01 DOI:10.1039/d4gc02211d
Changting Wen , Guojin Sun , Lang Liu , Jun Zhang , Mengyao She , Zheng Yang , Ping Liu , Shengyong Zhang , Jianli Li
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Abstract

Thiadiazole and selenadiazole derivatives are significant organic backbones widely utilized in drugs, bioactive molecules, and functional materials. A green and efficient one-pot synthetic methodology has been developed for the fabrication of thiadiazole/selenadiazole derivatives, which involves photocatalytic induced iodine substitution, oxydic aldehyde formation, and nucleophilic addition, resulting in C–S bond formation and hydrazylation, cyclization, and rearrangement, as well as dehydration. The present method includes good functional group tolerance, simple, mild, metal-free, and safe conditions that are in line with the principles of green chemistry, making this protocol an attractive strategy for the synthesis of bioactive molecules with thiadiazole/selenadiazole frameworks. Gratifyingly, the complanate and conjugate structures of the synthesized compounds ensured attractive fluorescent properties for successful application in biological cell imaging.

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光辅助绿色高效地构建噻二唑/硒二唑衍生物†。
噻二唑和硒二唑衍生物是重要的有机骨架,广泛应用于药物、生物活性分子和功能材料。该方法涉及光催化诱导碘取代、氧化醛形成和亲核加成,从而导致 C-S 键形成和肼化、环化、重排以及脱水。本方法具有良好的官能团耐受性,条件简单、温和、无金属且安全,符合绿色化学原理,因此是合成具有噻二唑/硒二唑框架的生物活性分子的一种有吸引力的策略。令人欣慰的是,合成化合物的共轭和共轭结构确保了其诱人的荧光特性,可成功应用于生物细胞成像。
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来源期刊
Green Chemistry
Green Chemistry 化学-化学综合
CiteScore
16.10
自引率
7.10%
发文量
677
审稿时长
1.4 months
期刊介绍: Green Chemistry is a journal that provides a unique forum for the publication of innovative research on the development of alternative green and sustainable technologies. The scope of Green Chemistry is based on the definition proposed by Anastas and Warner (Green Chemistry: Theory and Practice, P T Anastas and J C Warner, Oxford University Press, Oxford, 1998), which defines green chemistry as the utilisation of a set of principles that reduces or eliminates the use or generation of hazardous substances in the design, manufacture and application of chemical products. Green Chemistry aims to reduce the environmental impact of the chemical enterprise by developing a technology base that is inherently non-toxic to living things and the environment. The journal welcomes submissions on all aspects of research relating to this endeavor and publishes original and significant cutting-edge research that is likely to be of wide general appeal. For a work to be published, it must present a significant advance in green chemistry, including a comparison with existing methods and a demonstration of advantages over those methods.
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