C−H Methylthiolation/d3-Methylthiolation of Pyrazole Skeleton via Interrupted Pummerer Reaction

IF 2.7 4区 化学 Q1 CHEMISTRY, ORGANIC Asian Journal of Organic Chemistry Pub Date : 2024-12-17 DOI:10.1002/ajoc.202400639
Haofeng Shi, Fengxia Sun, Jialiang Wu, Jiaxin He, Yuli Sun, Yunfei Du
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Abstract

The reaction of a series of pyrazole derivatives with DMSO/ -DMSO-d6 and thionyl chloride conveniently afforded the 4-thiolated pyrazole products under metal-free conditions. This C−H functionalization/elelctrophilic thiolation process is postulated to involve the in situ generation of the electrophilic hypochlorothioite via interrupted Pummerer reaction, followed with the electrophilic methylthiolation of pyrazole skeleton.

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中断Pummerer反应中吡唑骨架的C−H甲基硫化/d3-甲基硫化
在无金属条件下,一系列吡唑衍生物与二甲基亚砜/-二甲基亚砜-d6 和亚硫酰氯反应,可以方便地得到 4-硫代吡唑产物。据推测,这种 C-H 功能化/亲电硫代过程是通过间断的普默尔反应在原位生成亲电的次硫代氯,然后对吡唑骨架进行亲电的甲硫醇化反应。
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来源期刊
CiteScore
4.70
自引率
3.70%
发文量
372
期刊介绍: Organic chemistry is the fundamental science that stands at the heart of chemistry, biology, and materials science. Research in these areas is vigorous and truly international, with three major regions making almost equal contributions: America, Europe and Asia. Asia now has its own top international organic chemistry journal—the Asian Journal of Organic Chemistry (AsianJOC) The AsianJOC is designed to be a top-ranked international research journal and publishes primary research as well as critical secondary information from authors across the world. The journal covers organic chemistry in its entirety. Authors and readers come from academia, the chemical industry, and government laboratories.
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