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用于一锅法合成甲氧基取代硫杂蒽鎓盐的傅-克方法

Friedel-Crafts approach to the one-pot synthesis of methoxy-substituted thioxanthylium salts.

作者信息

Tanaka Kenta, Tanaka Yuta, Kishimoto Mami, Hoshino Yujiro, Honda Kiyoshi

机构信息

Graduate School of Environment and Information Sciences, Yokohama National University, Tokiwadai, Hodogaya-ku, Yokohama 240-8501, Japan.

出版信息

Beilstein J Org Chem. 2019 Sep 5;15:2105-2112. doi: 10.3762/bjoc.15.208. eCollection 2019.

DOI:10.3762/bjoc.15.208
PMID:31579074
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6753671/
Abstract

An efficient synthesis of methoxy-substituted thioxanthylium salts has been developed. The reaction of diaryl sulfides with benzoyl chlorides in the presence of TfOH smoothly proceeded to give the desired thioxanthylium salts in good yields. In their UV-vis spectra, the maximum absorption wavelengths of methoxy-functionalized thioxanthylium salts were observed at around 460 nm, which show a drastic red shift compared to the parent thioxanthylium salts. The present reaction provides a versatile access to functionalized thioxanthylium salts, and therefore it constitutes a promising tool for the synthesis of biologically and photochemically active molecules.

摘要

已开发出一种高效合成甲氧基取代硫杂蒽鎓盐的方法。二芳基硫醚与苯甲酰氯在三氟甲磺酸(TfOH)存在下的反应顺利进行,以良好的产率得到所需的硫杂蒽鎓盐。在它们的紫外可见光谱中,观察到甲氧基官能化硫杂蒽鎓盐的最大吸收波长在460nm左右,与母体硫杂蒽鎓盐相比显示出显著的红移。本反应为官能化硫杂蒽鎓盐提供了一种通用的合成方法,因此它构成了一种用于合成生物和光化学活性分子的有前景的工具。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5d78/6753671/329ac8ec2f9b/Beilstein_J_Org_Chem-15-2105-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5d78/6753671/a75d691cd747/Beilstein_J_Org_Chem-15-2105-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5d78/6753671/db2864110d4c/Beilstein_J_Org_Chem-15-2105-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5d78/6753671/f7b93d6b56c5/Beilstein_J_Org_Chem-15-2105-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5d78/6753671/aef52249e738/Beilstein_J_Org_Chem-15-2105-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5d78/6753671/71ca84e5860b/Beilstein_J_Org_Chem-15-2105-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5d78/6753671/a6bf771d81e1/Beilstein_J_Org_Chem-15-2105-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5d78/6753671/329ac8ec2f9b/Beilstein_J_Org_Chem-15-2105-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5d78/6753671/a75d691cd747/Beilstein_J_Org_Chem-15-2105-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5d78/6753671/db2864110d4c/Beilstein_J_Org_Chem-15-2105-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5d78/6753671/f7b93d6b56c5/Beilstein_J_Org_Chem-15-2105-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5d78/6753671/aef52249e738/Beilstein_J_Org_Chem-15-2105-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5d78/6753671/71ca84e5860b/Beilstein_J_Org_Chem-15-2105-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5d78/6753671/a6bf771d81e1/Beilstein_J_Org_Chem-15-2105-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5d78/6753671/329ac8ec2f9b/Beilstein_J_Org_Chem-15-2105-g007.jpg

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Preparation, Structure, and Redox Reactions of Nine-Membered Cyclic Peroxides: A Novel Electrochromic System Undergoing Reversible Extrusion and Trapping of O(2) This work was supported by the Ministry of Education, Science, and Culture, Japan (No. 10146101). Financial support by the Izumi Science and Technology Foundation and by a Research Grant from the Iwatani Naoji Foundation (T.S.) are gratefully acknowledged. J.N. thanks JSPS Research Fellowships for Young Scientists. We thank Prof. Tamotsu Inabe (Hokkaido University) for the use of facilities to analyze the X-ray structures. Technical support by Mr. Kenji Watanabe and Dr. Eri Fukushi (GC-MS & NMR Laboratory, Faculty of Agriculture, Hokkaido University) is gratefully acknowledged.九元环状过氧化物的制备、结构及氧化还原反应:一种经历氧气可逆挤出和捕获的新型电致变色体系 本研究得到日本文部科学省(编号10146101)的支持。泉科学技术基金会以及岩谷直治基金会的研究资助(T.S.)在此表示衷心感谢。J.N.感谢日本学术振兴会青年科学家研究奖学金。我们感谢北海道大学的稻田保教授允许使用分析X射线结构的设备。渡边健二先生和福士绘里博士(北海道大学农学院GC-MS & NMR实验室)提供的技术支持在此表示衷心感谢。
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