Chinese Journal of Organic Chemistry >
Recent Progress in the Synthesis of 2-Benzofuran-1(3H)-one
Received date: 2021-09-03
Revised date: 2021-11-07
Online published: 2021-11-25
Supported by
National Natural Science Foundation of China(21971025); Natural Science Foundation of Zhejiang Province(LY21B020001)
2-Benzofuran-1(3H)-ones (isobenzofuranons) are multi-function precursors toward a variety of cyclic compounds as isobenzofuranon structure is ubiquitous in many natural products. Due to its extensive biological activity and wide application in medicinal chemistry, the preparation of these compounds has attracted great attention. In this paper, our and other research groups' work on the synthesis of isobenzofuranone in recent ten years from three aspects of transition metal catalytic synthesis, acid-base catalytic synthesis and other synthesis methods is summarized.
Key words： isobenzofuranone; derivative; synthetical method
Tingting Gong , Zhibin Chen , Miaochang Liu , Jiang Cheng . Recent Progress in the Synthesis of 2-Benzofuran-1(3H)-one[J]. Chinese Journal of Organic Chemistry, 2022 , 42(4) : 1085 -1100 . DOI: 10.6023/cjoc202109006
| [1] | Karmakar, R.; Pahari, P.; Mal, D. Chem. Rev. 2014, 114, 6213. |
| [2] | Ray, S.-K.; Sadhu, M.-M.; Biswas, R.-G.; Unhale, R.-A.; Singh, V.-K. Org. Lett. 2019, 21, 417. |
| [3] | Pan, Y.-L.; Zheng, H.-L.; Wang, J.; Yang, C.; Li, X.; Cheng, J.-P. ACS Catal. 2020, 10, 8069 |
| [4] | Huang, L.-J.; Wang, S.; Ma, F.; Zhang, Y.; Peng, Y.-C.; Xing, C.-H.; Feng, Y.-P.; Wang, X.-L.; Peng, Y. Pharmacol. Res. 2018, 135, 201. |
| [5] | Huang, X.-Z.; Yun, Z.; Guan, X.-L.; Kai, T.; Guo, J.-M.; Wang, H.-B.; Fu, G.-M. Molecules 2012, 17, 4219. |
| [6] | Lan, W.-J.; Liu, W.; Liang, W.-L.; Xu, Z.; Le, X.; Xu, J.; Lam, C.-K.; Wang, L.-Y. Mar. Drugs 2014, 12, 4188. |
| [7] | Yue, J.-M.; Xu, J.; Zhao, Y.; Sun, H.-D.; Lin, Z.-W. J. Nat. Prod. 1997, 60, 1031. |
| [8] | Rahman, M.-M.; Gray, A.-I. Phytochemistry 2005, 66, 1601. |
| [9] | Ma, F.-F.; Yuan, G.; Qiao, H.-L.; Hu, X.-J.; Chang, J.-B. J. Thromb. Thrombolysis 2012, 33, 64. |
| [10] | Tanaka, K.; Nishida, G.; Wada, A.; Noguchi, K. Angew. Chem., Int. Ed. 2004, 43, 6510. |
| [11] | Kitamura, M.; Ohkuma, T.; Inoue, S.; Sayo, N.; Kumobayashi, H. J. Am. Chem. Soc. 1988, 110, 629. |
| [12] | Phan, D.-H.-T.; Kim, B.; Dong, V.-M. J. Am. Chem. Soc. 2009, 131, 15608. |
| [13] | Zhang, B.; Xu, M.-H.; Lin, G.-Q. Org. Lett. 2009, 11, 4712. |
| [14] | Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457. |
| [15] | Ye, Z.; Lü, G.; Wang, W.; Zhang, M.; Cheng, J. Angew. Chem., Int. Ed. 2010, 49, 3671. |
| [16] | Wei, Y.; Hu, P.; Zhang, M.; Su, W.-P. Chem. Rev. 2017, 117, 8864. |
| [17] | Renzetti, A.; Nakazawa, H.; Li, C.-J. RSC Adv. 2016, 6, 40626. |
| [18] | Zhu, Y.-Q.; Li, J.-X.; Han, T.-F.; He, J.-L.; Zhu, K. Eur. J. Org. Chem. 2017, 2017, 806. |
| [19] | Danoun, G.; Mamone, P.; Gooßen, L.-J. Chem.-Eur. J. 2013, 19, 17287. |
| [20] | Liu, Y.; Yang, Y.-D.; Shi, Y.; Wang, X.-J.; Zhang, L.-Q.; Cheng, Y.-Y.; You, J.-S. Organometallics 2016, 35, 1350. |
| [21] | Han, W.-J.; Pu, F.; Fan, J.; Liu, Z.-W.; Shi, X.-Y. Adv. Synth. Catal. 2017, 359, 3520. |
| [22] | Qiu, Y.; Kong, W.-J.; Struwe, J.; Sauermann, N.; Rogge, T.; Scheremetjew, A.; Ackermann, L. Angew. Chem., Int. Ed. 2018, 57, 5828. |
| [23] | Lin, S.-H.; Lu, X.-Y. J. Org. Chem. 2007, 72, 9757. |
| [24] | Yamamoto, T.; Ohta, T.; Ito, Y. Org. Lett. 2005, 7, 4153. |
| [25] | Ye, Z.-S.; Qian, P.-C.; Lü, G.-L.; Luo, F.; Cheng, J. J. Org. Chem. 2010, 75, 6043. |
| [26] | Luo, F.; Pan, S.; Pan, C.-D.; Qian, P.-C.; Cheng, J. Adv. Synth. Catal. 2011, 353, 320. |
| [27] | Lin, H.; Sun, X.-W. Tetrahedron Lett. 2008, 49, 5343. |
| [28] | Yuan, S.; Zhang, D.-Q.; Zhang, J.-Y.; Yu, B.; Liu, H.-M. Org. Lett. 2020, 22, 814. |
| [29] | Chuc, L.-T.-N.; Nguyen, T.-A.-H.; Hou, D.-R. Org. Biomol. Chem. 2020, 18, 2758. |
| [30] | Liang, X.; Xiong, M.-T.; Zhu, H.-P.; Shi, K.-Q.; Zhou, Y.-F.; Pan, Y.-J. Org. Lett. 2020, 22, 9568. |
| [31] | Nandi, D.; Ghosh, D.; Chen, S.-J.; Kuo, B.-C.; Lee, H.-M. J. Org. Chem. 2013, 78, 3445. |
| [32] | Shi, S.; Chen, C.-H.; Chai, Y.; Zhang, L.-T.; Li, J.-W.; Liu, B.; Liu, Y.-J.; Zeng, M.-H. J. Org. Chem. 2019, 84, 9161. |
| [33] | Fan, J.; Wang, P.-M.; Wang, J.-N.; Zhao, X.; Liu, Z.-W.; Wei, J.-F.; Shi, X.-Y. Sci. China Chem. 2018, 61, 153. |
| [34] | Fardpour, M.; Darvish, A.; Kianmehr, E.; Kharat, A.-N. Tetrahedron Lett. 2018, 60, 699. |
| [35] | Ackermann, L.; Pospech, J. Org. Lett. 2011, 13, 4153. |
| [36] | Miura, H.; Tsutsui, K.; Wada, K.; Shishido, T. Chem. Commun. 2015, 51, 1654. |
| [37] | Yang, Y.; Rioux, R.-M. Chem. Commun. 2011, 47, 6557. |
| [38] | Zhao, H.; Zhang, T.; Yan, T.; Cai, M.-Z. J. Org. Chem. 2015, 80, 8849. |
| [39] | Bechtoldt, A.; Baumert, M.-E.; Vaccaro, L.; Ackermann, L. Green Chem. 2018, 20, 398. |
| [40] | Dana, S.; Dey, P.; Patil, S.-A.; Baidya, M. Chem.-Asian J. 2020, 15, 564. |
| [41] | Mandal, A.; Garai, B.; Dana, S.; Bera, R.; Baidya, M. Chem.-Asian J. 2020, 15, 4009. |
| [42] | Cabrera, J.-M.; Tauber, J.; Krische, M.-J. Angew. Chem., Int. Ed. 2018, 57, 1390. |
| [43] | Qiu, Y.; Stangier, M.; Ackermann, L. Angew. Chem., Int. Ed. 2018, 57, 14179. |
| [44] | Xiong, Y.-S.; Zhang, B.; Yu, Y.; Weng, J.; Lu, G. J. Org. Chem. 2019, 84, 13465. |
| [45] | Domínguez, G.; Pérez-Castells, J. Chem. Soc. Rev. 2011, 40, 3430. |
| [46] | Amatore, M.; Aubert, C. Eur. J. Org. Chem. 2015, 2015, 265. |
| [47] | Lledó, A.; Pla-Quintana, A.; Roglans, A. Chem. Soc. Rev. 2016, 45, 2010. |
| [48] | Méndez-Gálvez, C.; Böhme, M.; Leino, R.; Savela, R. Eur. J. Org. Chem. 2020, 2020, 1708. |
| [49] | Gandhi, S.; Baire, B. Adv. Synth. Catal. 2020, 362, 2651. |
| [50] | Jia, B.; Yang, Y.-H.; Jin, X.-Q.; Mao, G.-L.; Wang, C.-Y. Org. Lett. 2019, 21, 6259. |
| [51] | Maia, A.; Siqueira, R.-P.; Oliveira, F.; Ferreira, J.-G.; Teixeira, R.-R. Bioorg. Med. Chem. Lett. 2016, 26, 2810. |
| [52] | Mola, A.-D.; Filosa, R.; Massa, A. Molbank 2020, 2020, M1124. |
| [53] | Singha, M.; Maji, M.; Gupta, M.; Majhi, S.; Basak, A. Tetrahedron Lett. 2019, 60, 945. |
| [54] | Limaye, R.-A.; Kumbhar, V.-B.; Natu, A.-D.; Paradkar, M.-V.; Honmore, V.-S.; Chauhan, R.-R.; Gample, S.-P.; Sarkar, D. Bioorg. Med. Chem. Lett. 2013, 23, 711. |
| [55] | Li, J.; Chin, E.; Lui, A.-S.; Chen, L.-J. Tetrahedron Lett. 2010, 51, 5937. |
| [56] | Yang, X.-Y.; Xu, X.-Q.; Wang, X.-K.; Zheng, Z.-B.; Zhao, G.-M.; Li, S. Synth. Commun 2014, 44, 1780. |
| [57] | Fan, L.-L.; Luo, B.-L.; Luo, Z.-F.; Zhang, L.; Fan, J.-D.; Xue, W.; Tang, L.; Li, Y. Z. Naturforsch., B 2019, 74, 811. |
| [58] | Guo, T.; Wang, H.-J.; Cao, C.-C.; Chen, K.-H.; Liu, Y.; Zhang, P.-K.; Zhao, Y.-H.; Ma, Y.-C. Eur. J. Org. Chem. 2020, 24, 3613. |
| [59] | Du, Z.-H.; Xu, Q.-J.; Gu, G.-X. J. Saudi Chem. Soc. 2020, 24, 545. |
| [60] | Nakamura, Y.; Yoshida, S.; Hosoya, T. Chem. Lett. 2017, 46, 858. |
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