Synthesis of p-Alkoxy Phenol and Its Application after Dearomatization

doi:10.6023/cjoc202209012

Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (6): 2239-2244.DOI: 10.6023/cjoc202209012 Previous Articles Next Articles

对烷氧基酚的合成及其去芳构化后的合成应用

户晓兢^a, 郭斐翔^a, 朱润青^b, 周柄棋^b, 张涛^b, 房立真^b^,^*()

a 新乡医学院第三附属医院河南新乡 453003
b 新乡医学院药学院河南新乡 453003

收稿日期:2022-09-11 修回日期:2022-11-09 发布日期:2022-12-14
基金资助:
河南省科技厅高等学校学科创新引智基地(HNGD2021047); 河南省教育厅高等学校重点科研(21A350008)

Synthesis of p-Alkoxy Phenol and Its Application after Dearomatization

Xiaojing Hu^a, Feixiang Guo^a, Runqing Zhu^b, Bingqi Zhou^b, Tao Zhang^b, Lizhen Fang^b,*()

a The Third Affiliated Hospital of Xinxiang Medical University, Xinxiang, Henan 453003
b School of Pharmacy, Xinxiang Medical University, Xinxiang, Henan 453003

Received:2022-09-11 Revised:2022-11-09 Published:2022-12-14
Contact: * E-mail: 2002flz@163.com
Supported by:
Project from University Discipline Innovation and Talent Introduction Base of Science and Technology Department of Henan Province(HNGD2021047); Key Scientific Research Project of Henan Provincial Department of Education(21A350008)

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Abstract

p-Alkoxy phenol (p-AOPs) compounds were obtained by one-step selective hydroxylation of alkoxyl-aryl ethers with the transition metal ruthenium(II) as catalyst and [bis(trifluoroacetoxy)iodo]benzene (PIFA) as oxidant. These p-AOPs could be easily converted to quinone monoacetals (QMAs) after dearomatization. Condensation of the QMAs with β-naphthols provided polycyclic benzofurans which have a wide application prospect. The protocol established in this paper offered a facile and reliable way for the synthesis of these important compounds.

Key words: transition metal catalysis, regioselectivity hydroxylation, C—H activation, p-alkoxy phenol

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Xiaojing Hu, Feixiang Guo, Runqing Zhu, Bingqi Zhou, Tao Zhang, Lizhen Fang. Synthesis of p-Alkoxy Phenol and Its Application after Dearomatization[J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2239-2244.

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Fig. & Tab. 6

Figure 1. Drugs containing the basic structure of p-alkoxy phenyl phenol/ether.

Figure 2. Compound a with two state emission characteristics and molecular engineering raw material b

Scheme 1. Traditional synthesis methods (a, b) and current methods (c)

Table 1. Extension of substrates with different substituents on the benzene ring

Scheme 2. Synthesis of QMAS by dearomatization of p-AOPs

Table 2. Tetracyclic benzofuran compounds were synthesized by [3+2] cyclization with QMAs as substrate

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对烷氧基酚的合成及其去芳构化后的合成应用

Synthesis of p-Alkoxy Phenol and Its Application after Dearomatization

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