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2023 , Vol. 43 >Issue 2: 379 - 410

DOI: https://doi.org/10.6023/cjoc202207015

综述与进展

β-萘酚α位反应的研究进展

  • 刘静 ,
  • 陈锦涛 ,
  • 刘婷婷 ,
  • 刘佳 ,
  • 曾要富
展开
  • 南华大学衡阳医学院 药学院 湖南衡阳 421000
†共同第一作者

收稿日期: 2022-07-07

  修回日期: 2022-08-22

  网络出版日期: 2022-10-14

基金资助

湖南省大学生创新创业课题(S202210555288); 湖南省大学生创新创业课题(S202110555254); 南华大学大学生创新创业课题(X202210555181)

收起

Recent Advances in the Reactions of β-Naphthol at α-Position

  • Jing Liu ,
  • Jintao Chen ,
  • Tingting Liu ,
  • Jia Liu ,
  • Yaofu Zeng
Expand
  • School of Pharmaceutical Science, Hengyang Medical School, University of South China, Hengyang, Hunan 421000
†(These authors contributed equally to this work).
* Corresponding author.

Received date: 2022-07-07

  Revised date: 2022-08-22

  Online published: 2022-10-14

Supported by

Undergraduate Training Programs for Innovative and Entrepreneurship in Hunan Province(S202210555288); Undergraduate Training Programs for Innovative and Entrepreneurship in Hunan Province(S202110555254); Innovation and Entrepreneurship for College Students of University of South China(X202210555181)

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摘要

β-萘酚是有机合成中一种重要的合成子, 其α位化学性质活泼, 可参与多种化学反应, 受到了化学家的广泛关注. β-萘酚的α位可以发生多种化学转化, 如烷基化、芳基化、环化、胺化和卤化等, 利用这些化学反应可以构建结构多样化且具有不同生物活性的萘酚衍生物. 这些萘酚衍生物既可以作为天然活性药物的关键骨架, 也可以用于制备化学合成中的重要中间体. 基于近年来β-萘酚α位的化学反应层出不穷, 主要从β-萘酚α位碳-碳键和碳-杂键(C-N, C-O, C-X, C-S, C-P)的构建来对β-萘酚α位的相关反应进行了综述.

关键词： β-萘酚; α位; 碳-碳键; 碳-杂键

本文引用格式

刘静 , 陈锦涛 , 刘婷婷 , 刘佳 , 曾要富 . β-萘酚α位反应的研究进展[J]. 有机化学, 2023 , 43(2) : 379 -410 . DOI: 10.6023/cjoc202207015

Abstract

β-Naphthol is an important synthon in organic synthesis and can participate in various chemical reactions due to its active chemical property at α-site, which has attracted a great attention from chemists. β-Naphthol can undergo various chemical transformations at α-position, such as alkylation, arylation, cyclization, amination, halogenation and so on, which can be used to construct structurally diverse naphthol derivatives with various biological activities. These naphthol derivatives can be used not only as the privileged skeletons of natural active drugs, but also as the building blocks for the preparation of the important intermediates in chemical synthesis. In recent years, chemical reactions based on β-naphthol at α-site have emerged one after another. The reactions of β-naphthol at α-position are reviewed from the aspects of C-C, C-N, C-O, C-X, C-S, C-P bond constructions and so on.

Key words： β-naphthol; α-position; C-C bond; C-X bond

参考文献

[1]
Zhu, M.; Wang, D.-C.; Xie, M.-S.; Qu, G.-R.; Guo, H.-M. Chem.-Eur. J. 2018, 24, 15512.
[2]
Niu, L.-F.; Xin, Y.-C.; Wang, R.-L.; Jiang, F.; Xu, P.-F.; Hui, X.-P. Synlett 2010, 765.
[3]
Montesinos-Magraner, M.; Cantón, R.; Vila, C.; Blay, G.; Fernández, I.; Mu?oz, M. C.; Pedro, J. R. RSC Adv. 2015, 5, 60101.
[4]
Kaya, U.; Chauhan, P.; Mahajan, S.; Deckers, K.; Valkonen, A.; Rissanen, K.; Enders, D. Angew. Chem., Int. Ed. 2017, 56, 15358.
[5]
Li, C.-Y.; Xiang, M.; Zhang, J.; Li, W.-S.; Zou, Y.; Tian, F.; Wang, L.-X. Org. Biomol. Chem. 2021, 19, 7690.
[6]
Singh, R. K.; Dhiman, A.; Chaudhary, S.; Prasad, D. N.; Kumar, S. Curr. Org. Chem. 2020, 24, 487.
[7]
Li, G.-T.; Gu, Q.; You, S.-L. Chem. Sci. 2015, 6, 4273.
[8]
Bai, P.; Li, X.; Zhu, L.; Li, X. Petrochem. Technol. 2005, 34, 891. (in Chinese)
[8]
(白鹏, 李晓峰, 朱良伟, 李鑫钢, 石油化工, 2005, 34, 891.)
[9]
Li, Z.; Feng, C.-L.; Hei, L.-Y.; Gui, J.-Z.; Liu, D.-S. Chin. J. Synth. Chem. 2015, 23, 1074. (in Chinese)
[9]
(李珍, 冯翠兰, 黑莉楹, 桂建舟, 刘道胜, 合成化学 2015, 23, 1074.)
[10]
Cai, H.; Ouyang, K.; Yang, N. Chin. J. Org. Chem. 2019, 39, 1456. (in Chinese)
[10]
(蔡瀚, 欧阳昆冰, 阳年发, 有机化学, 2019, 39, 1456.)
[11]
Dou, Y.; Huang, X.; Wang, H.; Yang, L.; Li, H.; Yuan B.; Yang, G. Green Chem. 2017, 19, 2491.
[12]
Parumala, S. K. R.; Peddinti, R. K. Green Chem. 2015, 17, 4068.
[13]
Wang, H.-H.; Shi, T.; Gao, W.-W.; Wang, Y.-Q.; Li, J.-F.; Jiang, Y.; Hou, Y.-S.; Chen, C.; Peng, X.; Wang, Z. Chem.-Asian J. 2017, 12, 2675.
[14]
Jia, L.; Gao, S.; Xie, J.; Luo, M. Adv. Synth. Catal. 2016, 358, 3840.
[15]
Jia, L.; Tang, Q.; Luo, M.; Zeng, X. J. Org. Chem. 2018, 83, 5082.
[16]
Adachi, K.; Ohira, Y.; Tomizawa, G.; Ishihara, S.; Oishi, S. J. Fluorine Chem. 2003, 120, 173.
[17]
Araki, K.; Katagiri, T.; Inoue, M. J. Fluorine Chem. 2014, 157, 41.
[18]
Li, J.-Z.; Mei, L.; Cai, X.-E.; Zhang, C.-C.; Cao, T.-T.; Huang, X.-J.; Liu, Y.-L.; Wei, W.-T. Adv. Synth. Catal. 2011, 353, 2691.
[19]
Yu, X.-C.; Zheng, Y.-N.; Zhang, J.-H.; Zhang, J.; Liu, F.-L.; Tang, K.; Li, T.; Wei, W.-T. ACS Sustainable Chem. Eng. 2022, 10, 6057.
[20]
Li, L.; Li, J.-Z.; Sun, Y.-B.; Luo, C.-M.; Qiu, H.; Tang, K.; Liu, H.; Wei, W.-T. Org. Lett. 2022, 24, 4704
[21]
Li, S.; Yang, X.; Wang, Y.; Zhou, H.; Zhang, B.; Huang, G.; Zhang, Y.; Li, Y. Adv. Synth. Catal. 2019, 361, 4748.
[22]
Zhang, Y.; Li, S.; Zhu, Y.; Yang, X.; Zhou, H.; Li, Y. J. Org. Chem. 2020, 85, 6261.
[23]
Gao, H.; Xu, Q.-L.; Keene, C.; Yousufuddin, M.; Ess, D. H.; Kürti, L. Angew. Chem., Int. Ed. 2016, 55, 566.
[24]
Chaudhary, A. Mol. Diversity 2021, 25, 1211.
[25]
Vargas, J. A. M.; Day, D. P.; Burtoloso, A. C. B. Eur. J. Org. Chem., 2021, 2021, 741.
[26]
(a) Wang, H. Chirality 2010, 22, 827.
[26]
(b) Tkachenko, N. V.; Bryliakov, K. P. Mini-Rev. Org. Chem. 2019, 16, 392.
[26]
(c) An, J.; Bandini, M. Eur. J. Org. Chem. 2020, 2020, 4087.
[26]
(d) Montesinos-Magraner, M.; Vila, C.; Blay, G.; Pedro, J. R. Synthesis 2016, 48, 2151.
[27]
Das, B.; Reddy, C. R.; Sindhu, C.; Sudhakar, C.; Nagendra, S. Synthesis 2010, 3731.
[28]
Huo, C.; Kang, L.; Xu, X.; Jia, X.; Wang, X.; Yuan, Y.; Xie, H. Tetrahedron 2014, 70, 1055.
[29]
Wu, S.; Dong, J.; Zhou, D.; Wang, W.; Liu, L.; Zhou, Y. J. Org. Chem. 2019, 85, 14307.
[30]
Suzuki, N.; Tsuchihashi, S.; Nakata, K. Tetrahedron Lett. 2016, 57, 1456.
[31]
Shaterian, H. R.; Hosseinian, A.; Ghashang, M. Synth. Commun. 2008, 38, 3375.
[32]
Khazaei, A.; Abbasia, F.; Moosavi-Zare, A. R. RSC Adv. 2014, 4, 1388.
[33]
Ghorbani-Choghamarani, A.; Rashidimoghadam, S. Chin. J. Catal. 2014, 35, 1024.
[34]
Gong, K.; Wang, H.; Ren, X.; Wang, Y.; Chen, J. Green Chem. 2015, 17, 3141.
[35]
Darbandi, H.; Kiyani H. Curr. Organocatal. 2020, 7, 34.
[36]
Lohar, T.; Mane, A.; Kamat, S.; Salunkhe R. Polycyclic Aromat. Compd. 2018, 40, 1210.
[37]
Yu, L.; Xie, X.; Wu, S.; Wang, R.; He, W.; Qin, D.; Liu, Q.; Jing, L. Tetrahedron Lett. 2013, 54, 3675.
[38]
Lan, J.-P.; Lu, Y.-N.; Chen, K.-W.; Jiang, F.; Gao, F.; Zhang, Y.-C.; Shi, F. Synthesis 2020, 52, 3684.
[39]
An, J.; Lombardi, L.; Grilli, S.; Bandini, M. Org. Lett. 2018, 20, 7380.
[40]
Jin, M.; Ren, W.; Qian, D.-W.; Yang, S.-D. Org. Lett. 2018, 20, 7015.
[41]
Das, B. G.; Shah, S.; Das, A.; Singh, V. K. Org. Lett. 2021, 23, 6262.
[42]
Yang, B.; Zhai, X.; Feng, S.; Shao, Z. Org. Chem. Front. 2018, 5, 2794.
[43]
Tang, S.-B.; Tu, H.-F.; Zhang, X.; You, S.-L. Org. Lett. 2019, 21, 6130.
[44]
Fu, Z.; Zhu, J.; Guo, S.; Lin, A. Chem. Commun. 2021, 57, 1262.
[45]
Wang, D.-C.; Cheng, P.-P.; Yang, T.-T.; Wu, P.-P.; Qu, G.-R.; Guo, H.-M. Org. Lett. 2021, 23, 7865.
[46]
Ding, L.; Wu, W.-T.; Zhang, L.; You, S.-L. Org. Lett. 2020, 22, 5861.
[47]
Zhang, Y.; Wang, H.; Yu, H.; Sun, X. RSC Adv. 2022, 12, 11967.
[48]
Qian, X.; Han, J.; Wang, L. Tetrahedron Lett. 2016, 57, 607.
[49]
Ghosh, M. K.; Rzymkowski, J.; Kalek, M. Chem.-Eur. J. 2019, 25, 1.
[50]
Reiss, H.; Shalit, H.; Vershinin, V.; More, N. Y.; Forckosh, H.; Pappo, D. J. Org. Chem. 2019, 84, 7950.
[51]
Chen, Y.-H.; Cheng, D.-J.; Zhang, J.; Wang, Y.; Liu, X.-Y.; Tan, B. J. Am. Chem. Soc. 2015, 137, 15062.
[52]
Wang, J.-Z.; Zhou, J.; Xu, C.; Sun, H.; Kürti, L.; Xu, Q.-L. J. Am. Chem. Soc. 2016, 138, 5202.
[53]
Moliterno, M.; Cari, R.; Puglisi, A.; Antenucci, A.; Sperandio, C.; Moretti, E.; Sabato, A. D.; Salvio, R.; Bella, M. Angew. Chem. 2016, 128, 6635.
[54]
Coombs, G.; Sak, M. H.; Miller, S. J. Angew. Chem., Int. Ed. 2020, 132, 2897.
[55]
Utepova, I. A.; Nemytov, A. I.; Ishkhanian, V. A.; Chupakhin, O. N.; Charushin, V. N. Tetrahedron 2020, 76, 131391.
[56]
Wang, J.; Zhao, Y.; Gao, H.; Gao, G.-L.; Yang, C.; Xia, W. Asian J. Org. Chem. 2017, 6, 1402.
[57]
Tkachenko, N. V.; Bryliakov, K. P. Mini-Rev. Org. Chem. 2019, 16, 392.
[58]
Horibe, T.; Nakagawa, K.; Hazeyama, T.; Takeda, K.; Ishihara, K. Chem. Commun. 2019, 55, 13677.
[59]
Narute, S.; Parnes, R.; Toste, F. D.; Pappo, D. J. Am. Chem. Soc. 2016, 138, 16553.
[60]
Matsushita, M.; Kamata, K.; Yamaguchi, K.; Mizuno, N. J. Am. Chem. Soc. 2005, 127, 6632.
[61]
Yan, P.; Sugiyama, Y.; Takahashi, Y.; Kinemuchi, H.; Temma, T.; Habaue, S. Tetrahedron 2008, 64, 4325.
[62]
Tian, J.-M.; Wang, A.-F.; Yang, J.-S.; Zhao, X.-J.; Tu, Y.-Q.; Zhang, S.-Y.; Chen, Z.-M. Angew. Chem., Int. Ed. 2019, 58, 11023.
[63]
Wu, L.-Y.; Usman, M.; Liu, W.-B. Molecules 2020, 25, 852.
[64]
Qi, L.-W.; Li, S.; Xiang, S.-H.; Wang, J.; Tan, B. Nat. Catal. 2019, 2, 314.
[65]
He, Z.; Pulis, A. P.; Procter, D. J. Angew. Chem., Int. Ed. 2019, 58, 7813.
[66]
Kimura, T.; Watanabe, M.; Kashiwamura, G.; Sakurada, J.; Satoh, T. Synthesis 2013, 45, 659.
[67]
Wang, D.; Tong, X. Org. Lett. 2017, 19, 6392.
[68]
Deng, T.; Wang, H.; Cai, C. Eur. J. Org. Chem. 2015, 2015, 1569.
[69]
Narute, S.; Pappo, D. Org. Lett. 2017, 19, 2917.
[70]
Li, Z.; Peng, J.; He, C.; Xu, J.; Ren, H. Org. Lett. 2020, 22, 5768.
[71]
Liu, L.; Ji, X.; Dong, J.; Zhou, Y.; Yin, S.-F. Org. Lett. 2016, 18, 3138.
[72]
Kaicharla, T.; Roy, T.; Thangaraj, M.; Gonnade, R. G.; Biju, A. T. Angew. Chem., Int. Ed. 2016, 55, 10061.
[73]
Kaicharla, T.; Jacob, A.; Gonnade, R. G.; Biju, A. T. Chem. Commun. 2017, 53, 8219.
[74]
Jacob, A.; Roy, T.; Kaicharla, T.; Biju, A. T. J. Org. Chem. 2017, 82, 11269.
[75]
Zhao, H.; Shen, P.; Sun, D.; Zhai, H.; Zhao, Y. Front. Chem. 2021, 9, 711257.
[76]
Jin, R.; Patureau, F. W. Org. Lett. 2016, 18, 4491.
[77]
Conde, A.; Sabenya, G.; Rodríguez, M.; Postils, V.; Luis, J. M.; Díaz-Requejo, M. M.; Costas, M.; Pérez, P. J. Angew. Chem. 2016, 128, 6640.
[78]
Wang, D.-K.; Li, L.-B.; Liu, F.-L.; Qiu, H.; Li, J.-Z.; Zhang, J.; Deng, C.; Wei, W.-T. ACS Cent. Sci. 2022, 8, 1028.
[79]
Liu, L.-X. Curr. Org. Chem. 2010, 14, 1099.
[80]
Yu, F.; Xu, H.; Asiri, A. M.; Marwani, H. M.; Zhang, Z. Synth. Commun. 2019, 49, 704.
[81]
Nan, J.; Liu, J.; Zheng, H.; Zuo, Z.; Hou, L.; Hu, H.; Wang, Y.; Luan, X. Angew. Chem., Int. Ed. 2015, 54, 2356.
[82]
Yi, J.-C.; Tu, H.-F.; You, S.-L. Org. Biomol. Chem. 2018, 16, 8700.
[83]
Bai, L.; Luo, X.; Ge, Y.; Wang, H.; Liu, J.; Wang, Y.; Luan, X. CCS Chem. 2022, 4, 1054.
[84]
Shomali, A.; Valizadeh, H.; Noorshargh, S. Lett. Org. Chem. 2017, 14, 409.
[85]
Dong, W.; Ren, H. Chin. J. Chem. Educ. 2020, 41, 56. (in Chinese)
[85]
(董伟, 任红, 化学教育, 2020, 41, 56.)
[86]
Liu, T.-T.; Yan, J.-Z.; Cheng, X.-W.; Duan, P.; Zeng, Y.-F. J. Chem. Res. 2021, 45, 486.
[87]
Anjaiah, C.; Nagamani, M.; Lincoln, C. A.; Ashok, D. Russ. J. Gen. Chem. 2017, 87, 2930.
[88]
Xiao, F.; Tian, J.; Xing, Q.; Huang, H.; Deng, G.-J.; Liu, Y. Sustainable Chem. 2017, 2, 428.
[89]
Wang, D.; Guo, S.; Zhang, R.; Lin, S.; Yan, Z. RSC Adv. 2016, 6, 54377.
[90]
Xiao, F.; Chen, S.; Tian, J.; Huang, H.; Liu, Y.; Deng, G.-J. Green Chem. 2016, 18, 1538.
[91]
Zhou, K.; Chen, M.; Yao, L.; Wu, J. Org. Chem. Front. 2018, 5, 371.
[92]
Zhang, S.-S.; Xue, J.; Gu, Q.; Jiang, X.; You, S.-L. Org. Biomol. Chem. 2021, 19, 8761.
[93]
Ghosh, T; Mukherjee, N.; Ranu, B. C. ACS Omega 2018, 3, 17540.
[94]
Lima, D. B.; Santos, P. H. V.; Fiori, P.; Badshah, G.; Luz, E. Q.; Seckler, D.; Rampon, D. S. ChemistrySelect 2019, 4, 13558.
[95]
Zhang, Y.; Liao, Y.; Liu, X.; Xu, X.; Lin, L.; Feng, X. Chem. Sci. 2017, 8, 6645.
[96]
Yin, Q.; Wang, S.-G.; Liang, X.-W.; Gao, D.-W.; Zheng, J.; You, S.-L. Chem. Sci. 2015, 6, 4179.
[97]
Zhang, Z.; Sun, Q.; Xu, D.; Xia, C.; Sun, W. Green Chem. 2016, 18, 5485.
[98]
Nahide, P. D.; Ramadoss, V.; Juárez-Ornelas, K. A.; Satkar, Y.; Ortiz-Alvarado, R.; Cervera-Villanueva, J. M. J.; Alonso-Castro á. J.; Zapata-Morales J. R.; Ramírez-Morales, M. A.; Ruiz-Padilla A. J.; Deveze-álvarez M. A.; Solorio-Alvarado C. R. Eur. J. Org. Chem. 2018, 2018, 485.
[99]
Satkar, Y.; Yera-Ledesma, L. F.; Mali, N.; Patil, D.; Navarro-Santos, P.; Segura-Quezada, L. A.; Ramírez-Morales, P. I.; Solorio-Alvarado C. R. J. Org. Chem. 2019, 84, 4149.
[100]
Segura-Quezada, A.; Satkar, Y.; Patil, D.; Mali, N.; Wrobel, K.; González, G.; Zárraga, R.; Ortiz-Alvarado, R.; Solorio-Alvarado C. R. Tetrahedron Lett. 2019, 60, 1551.
[101]
Egami, H.; Rouno, T.; Niwa, T.; Masuda, K.; Yamashita, K.; Hamashima, Y. Angew. Chem., Int. Ed. 2020, 59, 14101.
[102]
Blanco, G. A.; Baumgartner, M. T. New J. Chem. 2010, 34, 2306.
[103]
Xiong, B.; Li, M.; Liu, Y.; Zhou, Y.; Zhao, C.; Goto, M.; Yin, S.-F.; Han, L.-B. Adv. Synth. Catal. 2014, 356, 781.
[104]
Yuan, J.; Liu, Y.; Ge, Y.; Dong, S.; Song, S.; Yang, L.; Xiao, Y.; Zhang, S.; Qu, L. Chin. J. Org. Chem. 2021, 41, 4738. (in Chinese)
[104]
(袁金伟, 刘燕, 葛元元, 董少轩, 宋赛依, 杨亮茹, 肖咏梅, 张守仁, 屈凌波, 有机化学, 2021, 41, 4738.)
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