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通过由PhICl和NHSCN/KSeCN介导的氧化硫氰化或硒氰化反应合成4-官能化吡唑。

Synthesis of 4-functionalized pyrazoles via oxidative thio- or selenocyanation mediated by PhICl and NHSCN/KSeCN.

作者信息

Wu Jialiang, Shi Haofeng, Li Xuemin, He Jiaxin, Zhang Chen, Sun Fengxia, Du Yunfei

机构信息

Tianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, China.

Hebei Research Center of Pharmaceutical and Chemical Engineering, Hebei University of Science and Technology, Shijiazhuang 050018, China.

出版信息

Beilstein J Org Chem. 2024 Jun 28;20:1453-1461. doi: 10.3762/bjoc.20.128. eCollection 2024.

DOI:10.3762/bjoc.20.128
PMID:38952956
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11216092/
Abstract

A series of 4-thio/seleno-cyanated pyrazoles was conveniently synthesized from 4-unsubstituted pyrazoles using NHSCN/KSeCN as thio/selenocyanogen sources and PhICl as the hypervalent iodine oxidant. This metal-free approach was postulated to involve the in situ generation of reactive thio/selenocyanogen chloride (Cl-SCN/SeCN) from the reaction of PhICl and NHSCN/KSeCN, followed by an electrophilic thio/selenocyanation of the pyrazole skeleton.

摘要

使用NHSCN/KSeCN作为硫/硒氰基源，PhICl作为高价碘氧化剂，从4-未取代的吡唑方便地合成了一系列4-硫代/硒氰化吡唑。这种无金属方法被推测涉及从PhICl与NHSCN/KSeCN的反应中原位生成活性硫/硒氰基氯（Cl-SCN/SeCN），随后对吡唑骨架进行亲电硫/硒氰化反应。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9981/11216092/eb44d5069098/Beilstein_J_Org_Chem-20-1453-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9981/11216092/601f5682597e/Beilstein_J_Org_Chem-20-1453-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9981/11216092/f743a2cbd53a/Beilstein_J_Org_Chem-20-1453-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9981/11216092/84a52bcdb586/Beilstein_J_Org_Chem-20-1453-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9981/11216092/3ed079068afc/Beilstein_J_Org_Chem-20-1453-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9981/11216092/9a4e558ac66f/Beilstein_J_Org_Chem-20-1453-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9981/11216092/eb44d5069098/Beilstein_J_Org_Chem-20-1453-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9981/11216092/601f5682597e/Beilstein_J_Org_Chem-20-1453-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9981/11216092/f743a2cbd53a/Beilstein_J_Org_Chem-20-1453-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9981/11216092/84a52bcdb586/Beilstein_J_Org_Chem-20-1453-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9981/11216092/3ed079068afc/Beilstein_J_Org_Chem-20-1453-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9981/11216092/9a4e558ac66f/Beilstein_J_Org_Chem-20-1453-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9981/11216092/eb44d5069098/Beilstein_J_Org_Chem-20-1453-g007.jpg

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