研究论文

对烷氧基酚的合成及其去芳构化后的合成应用

  • 户晓兢 ,
  • 郭斐翔 ,
  • 朱润青 ,
  • 周柄棋 ,
  • 张涛 ,
  • 房立真
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  • 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

  网络出版日期: 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 ,
  • Feixiang Guo ,
  • Runqing Zhu ,
  • Bingqi Zhou ,
  • Tao Zhang ,
  • Lizhen Fang
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  • a The Third Affiliated Hospital of Xinxiang Medical University, Xinxiang, Henan 453003
    b School of Pharmacy, Xinxiang Medical University, Xinxiang, Henan 453003
* E-mail:

Received date: 2022-09-11

  Revised date: 2022-11-09

  Online published: 2022-12-14

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)

摘要

以过渡金属钌(II)为催化剂, 双三氟乙酰氧基碘苯(PIFA)为氧化剂, 通过一步反应在烷氧基芳基醚对位选择性地实现羟基化, 得到了对烷氧基苯酚(p-AOPs)类化合物. 该类化合物去芳构化后, 能方便地转化为醌单缩醛(QMAs), 进一步与β-萘酚缩合可得到一些具有广泛应用前景的多环苯并呋喃化合物, 为合成这类重要化合物提供了一种简洁可靠的途径.

本文引用格式

户晓兢 , 郭斐翔 , 朱润青 , 周柄棋 , 张涛 , 房立真 . 对烷氧基酚的合成及其去芳构化后的合成应用[J]. 有机化学, 2023 , 43(6) : 2239 -2244 . DOI: 10.6023/cjoc202209012

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.

参考文献

[1]
(a) Jiang, W.; Li, Y.; Wang, Z. Chem. Soc. Rev. 2013, 42, 6113.
[1]
(b) Stepien, M.; Gonka, E.; Zyla, M.; Sprutta, N. Chem. Rev. 2017, 117, 3479.
[1]
(c) Wang, C.; Dong, H.; Hu, W.; Liu, Y.; Zhu, D. Chem. Rev. 2012, 112, 2208.
[2]
Singh, D. K.; Jang, K.; Kim, J.; Lee, J.; Kim, I. ACS Comb. Sci. 2019, 21, 408.
[3]
Hu, X.; Nie, L.; Zhang, G.; Lei, A. Angew. Chem., Int. Ed. Engl. 2020, 59, 15238.
[4]
Saint-Denis, T. G.; Zhu, R. Y.; Chen, G.; Wu, Q. F.; Yu, J. Q. Science 2018, 359(6377), eaao4798.
[5]
Pilevar, A.; Hosseini, A.; Sekutor, M.; Hausmann, H.; Becker, J.; Turke, K.; Schreiner, P. R. J. Org. Chem. 2018, 83, 10070.
[6]
(a) Liu, Y.; Liu, S.; Xiao, Y. Beilstein J. Org. Chem. 2017, 13, 589.
[6]
(b) Inamoto, K.; Nozawa, K.; Yonemoto, M.; Kondo, Y. Chem. Commun. (Camb.) 2011, 47, 11775.
[6]
(c) Rayment, E. J.; Summerhill, N.; Anderson, E. A. J. Org. Chem. 2012, 77, 7052.
[7]
(a) Sinha, S. K.; Guin, S.; Maiti, S.; Biswas, J. P.; Porey, S.; Maiti, D. Chem. Rev. 2022, 122, 5682.
[7]
(b) Yamaguchi, J.; Yamaguchi, A. D.; Itami, K. Angew. Chem., Int. Ed. 2012, 51, 8960.
[8]
(a) Dong, J.; Liu, P.; Sun, P. J. Org. Chem. 2015, 80, 2925.
[8]
(b) Kim, K.; Choe, H.; Jeong, Y.; Lee, J. H.; Hong, S. Org. Lett. 2015, 17, 2550.
[9]
Jintoku, T. N. K.; Takaki, K.; Fujiwara, Y. Chem. Lett. 1990, 1687.
[10]
Zhu, R.; Sun, Q.; Li, J.; Li, L.; Gao, Q.; Wang, Y.; Fang, L. Chem. Commun. (Camb.) 2021, 57, 13190.
[11]
(a) Kamitanaka, T.; Tsunoda, Y.; Fujita, Y.; Dohi, T.; Kita, Y. Org. Lett. 2021, 23, 9025.
[11]
(b) Kobayashi, H.; Sasano, Y.; Kanoh, N.; Kwon, E.; Iwabuchi, Y. Eur. J. Org. Chem. 2016, 2016, 270.
[12]
Fang, L.; Lyu, Q.; Lu, C.; Li, H.; Liu, S.; Han, L. Adv. Synth. Catal. 2016, 358, 3196.
[13]
Jacob, A.; Roy, T.; Kaicharla, T.; Biju, A. T. J. Org. Chem. 2017, 82, 11269.
[14]
Liu, P.; Du, Y.; Song, L.; Shen, J.; Li, Q. Bioorg. Med. Chem. 2015, 23, 7079.
[15]
Mudduluru, H.; Hindupur, R. M.; Dubey, P. K.; Madhavaram, S.; Tatini, L.; Subbaraju, G. V. Lett. Org. Chem. 2011, 8, 234.
[16]
Sarma, P. K. S. WO 2012090219, 2012 [Chem. Abstr. 2012, 159, 639199].
[17]
Sarma, P. K. S. WO 2010127208, 2010 [Chem. Abstr. 2010, 153, 579940].
[18]
Yin, Z.; Zhang, J.; Wu, J.; Green, R.; Li, S.; Zheng, S. Org. Biomol. Chem. 2014, 12, 2854.
[19]
Gu, Y. G. WO 2008079610, 2008 [Chem. Abstr. 2008, 149,128642].
[20]
David, J. DE 2126169, 1972 [Chem. Abstr. 1972, 76, 72289].
[21]
Sahoo, S. R.; Sarkar, D. Tetrahedron Lett. 2020, 61, 151646.
[22]
Punna, S.; Meunier, S.; Finn, M. G. Org. Lett. 2004, 6, 2777.
[23]
Pelter, A.; Elgendy, S. M. A. J. Chem. Soc., 1993, 1891.
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