2-氨基吡啶在构建五元、六元氮稠环合成中的应用

doi:10.6023/cjoc202104011

摘要/Abstract

2-氨基吡啶是一类重要的合成子, 具有独特的双亲核结构, 可与酮、醛、酸、多官能团酯类以及卤代芳烃等化合物反应, 以构建五元、六元含氮稠杂环. 近年来, 基于2-氨基吡啶的成环反应倍受关注. 鉴于此, 以底物种类为分类依据, 重点综述了近5年来基于2-氨基吡啶构建咪唑并[1,2-a]吡啶、吡啶并[1,2-a]嘧啶合成方法的研究进展, 总结了其在有机合成方法学、药物合成和荧光探针等领域的应用, 并展望了基于2-氨基吡啶的绿色化成环及其应用的未来发展趋势.

关键词: 2-氨基吡啶, 咪唑并[1,2-a]吡啶, 吡啶并[1,2-a]嘧啶, 氮稠环化合物, C—N键构建, 逆合成分析

2-Aminopyridine is a significant synthetic synthon, with unique dual nucleophilic structure. It can react with ketones, aldehydes, acids, multifunctional esters, halogenated aromatics and other compounds to synthesize five- and six-member azaheterocycles. In recent years, the cyclization reactions based on 2-aminopyridines have been under the spotlight. According to the different types of substrates, the research progress on the synthesis of imidazo[1,2-a]pyridines and pyrido[1,2-a]pyri- midines based on 2-aminopyridines in the past 5 years is reviewed, and its applications in organic synthesis methodology, drug synthesis and fluorescent probes are summarized. Furthermore, the development trend of green cyclization and its application based on 2-aminopyridines in the future are prospected.

Key words: 2-aminopyridine, imidazo[1,2-a]pyridine, pyrido[1,2-a]pyrimidine, azaheterocycle, C—N bond formation, retro- synthetic analysis

引用此文

陈淇, 陈思鸿, 吴汉清, 曾晓晴, 陈伟清, 孙国星, 汪朝阳. 2-氨基吡啶在构建五元、六元氮稠环合成中的应用[J]. 有机化学, 2021, 41(9): 3482-3491.

Qi Chen, Sihong Chen, Hanqing Wu, Xiaoqing Zeng, Weiqing Chen, Guoxing Sun, Zhaoyang Wang. Application of 2-Aminopyridines in the Synthesis of Five- and Six-Membered Azaheterocycles[J]. Chinese Journal of Organic Chemistry, 2021, 41(9): 3482-3491.

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图/表 17

图式1. 2-氨基吡啶合成咪唑并[1,2-a]吡啶中咪唑环的逆合成分析

Scheme 1. Retrosynthetic analysis for the synthesis of imidazo[1,2-a]pyridine from 2-aminopyridine

图式2. 2-氨基吡啶和α-溴代苯乙酮合成2-芳基咪唑并[1,2-a]吡啶的反应机理

Scheme 2. Plausible mechanism for the synthesis of 2-arylimi- dazo[1,2-a]pyridines from 2-aminopyridines and α-bromoaceto- phenones

图式3. 微波辐射辅助α-溴代苯乙酮的合成及其与2-氨基吡啶的缩合反应

Scheme 3. Microwave radiation-assisted synthesis of α-bromo- acetophenone and its condensation reaction with 2-aminopyridine

图式4. 通过有机电化学合成法由2-氨基吡啶合成咪唑并[1,2-a]吡啶类化合物

Scheme 4. Synthesis of imidazo[1,2-a]pyridines from 2-amino- pyridine via organic electrochemical method

图式5. 2-氨基吡啶与炔丙醛合成咪唑并[1,2-a]吡啶类化合物

Scheme 5. Synthesis of imidazo[1,2-a]pyridines from 2-amino- pyridines and propargyl aldehydes

图式6. 2-氨基吡啶、芳香醛和末端炔烃合成咪唑[1,2-a]吡啶反应的机理简图

Scheme 6. Simple scheme of the plausible mechanism for the synthesis of imidazo[1,2-a]pyridines from 2-aminopyridines, aromatic aldehydes and terminal alkynes

图式7. 2-氨基吡啶和氯乙酸合成咪唑并[1,2-a]吡啶类化合物

Scheme 7. Synthesis of imidazo[1,2-a]pyridine compounds from 2-aminopyridine and chloroacetic acid

图式8. 2-氨基吡啶生成咪唑并[1,2-a]吡啶的成环反应

Scheme 8. Cyclization reaction of imidazo[1,2-a]pyridines from 2-aminopyridines

图式9. 2-氨基吡啶和肉桂醛合成2-芳基-3-甲酰基咪唑并[1,2-a]吡啶的反应机理

Scheme 9. Plausible mechanism for the synthesis of 2-aryl-3-formylimidazo[1,2-a]pyridines from 2-aminopyridines and cinnamaldehydes

图式10. 2-氨基吡啶合成吡啶并[1,2-a]嘧啶中嘧啶环的逆合成分析

Scheme 10. Retrosynthetic analysis for the synthesis of pyrido[1,2-a]pyrimidines from 2-aminopyridines

图式11. 由2-氨基吡啶类化合物和丙二酸二乙酯合成抗肾肿瘤类药物

Scheme 11. Synthesis of anti-kidney tumor drugs from 2-amino- pyridine type compound and diethyl malonate

图式12. 由2-氨基吡啶类化合物和丙二酸二(2,4,6-三氯苯基)酯合成HCV抑制剂

Scheme 12. Synthesis of HCV inhibitor from 2-aminopyridine type compound and bis(2,4,6-trichlorophenyl) malonate

图式13. 2-氨基吡啶和乙酰乙酸乙酯合成4H-吡啶并[1,2-a]嘧啶-4-酮的反应机理

Scheme 13. Plausible mechanism for the synthesis of 4H- pyrido[1,2-a]pyrimidin-4-ones from 2-aminopyridines and ethyl acetoacetates

图式14. 2-氨基吡啶和乙酰乙酸乙酯合成2H-吡啶并[1,2-a]嘧啶-2-酮的反应机理

Scheme 14. Plausible mechanism for the synthesis of 2H-pyri- do[1,2-a]pyrimidin-2-ones from 2-aminopyridines and ethyl acetoacetates

图式15. 2-氨基吡啶和α-羟甲基烯酸酯合成2H-吡啶并[1,2-a]嘧啶-2-酮的反应机理

Scheme 15. Plausible mechanism for the synthesis of 2H-pyri- do[1,2-a]pyrimidin-2-ones from 2-aminopyridines and α-hydro- xymethyl acrylates

图式16. 由酰胺与2-氨基吡啶合成3-酰基-4H-吡啶并[1,2-a]嘧啶-4-亚胺

Scheme 16. Synthesis of 3-acyl-4H-pyrido[1,2-a]pyrimidin- 4-imines from enaminones and 2-aminopyridines

图式17. 2-氨基吡啶生成吡啶并[1,2-a]嘧啶类化合物的成环反应

Scheme 17. Cyclization reaction of pyrido[1,2-a]pyrimidine compounds from 2-aminopyridines

参考文献 108

[1]	Kiefl, G. M.; Gulder, T. J. Am. Chem. Soc. 2020, 142, 20577. doi: 10.1021/jacs.0c10700
[2]	Cook, X. A. F.; de Gombert, A.; McKnight, J.; Pantaine, L. R. E.; Willis, M. C. Angew. Chem., Int. Ed. 2021, 60, 11068. doi: 10.1002/anie.v60.20
[3]	Khatua, H.; Das, S. K.; Roy, S.; Chattopadhyay, B. Angew. Chem., Int. Ed. 2021, 60, 304. doi: 10.1002/anie.v60.1
[4]	Ma, S. J.; Hill, C. K.; Olen, C. L.; Hartwig, J. F. J. Am. Chem. Soc. 2021, 143, 359. doi: 10.1021/jacs.0c11043
[5]	Bagdi, A. K.; Santra, S.; Monir, K.; Hajra, A. Chem. Commun. 2015, 51, 1555. doi: 10.1039/C4CC08495K
[6]	Pericherla, K.; Kaswan, P.; Pandey, K.; Kumar, A. Synthesis 2015, 47, 887. doi: 10.1055/s-00000084
[7]	Keiko, N. A.; Vchislo, N. V. Chem. Heterocycl. Compd. 2016, 52, 222. doi: 10.1007/s10593-016-1867-x
[8]	Mutai, T.; Muramatsu, T.; Yoshikawa, I.; Houjou, H.; Ogura, M. Org. Lett. 2019, 21, 2143. doi: 10.1021/acs.orglett.9b00455
[9]	Wu, Y. X.; Yuan, W.; Ji, H. Y.; Qin, Y. R.; Zhang, J.; Li, H. K.; Li, Y. H.; Wang, Y.; Sun, Y. F.; Liu, W. Dyes Pigm. 2017, 142, 330. doi: 10.1016/j.dyepig.2017.03.052
[10]	Yang, X.-Z.; Xu, B.; Shen, L.; Sun, R.; Xu, Y.-J.; Song, Y.-L.; Ge, J.-F. Anal. Chem. 2020, 92, 3517. doi: 10.1021/acs.analchem.0c00054
[11]	Thakur, A.; Pereira, G.; Patel, C.; Chauhan, V.; Dhaked, R. K; Sharma, A. J. Mol. Struct. 2020, 1206, 127686. doi: 10.1016/j.molstruc.2020.127686
[12]	Bin Sayeed, I.; Vishnuvardhan, M. V. P. S.; Nagarajan, A.; Kantevari, S.; Kamal, A. Bioorg. Chem. 2018, 80, 714. doi: 10.1016/j.bioorg.2018.07.026
[13]	Lawson, M.; Rodrigo, J.; Baratte, B. Robert, T.; Delehouze, C.; Lozach, O.; Ruchaud, S.; Bach, S.; Brion, J. D.; Alami, M.; Hamze, A. Eur. J. Med. Chem. 2016, 123, 105. doi: S0223-5234(16)30601-8 pmid: 27474927
[14]	Campos, J. F.; Scherrmann, M. M. C.; Berteina-Raboine, S. Green Chem. 2019, 21, 1531. doi: 10.1039/c8gc04016h
[15]	Rodriguez, J. C.; Maldonado, R. A.; Ramirez-Garcia, G.; Cervantes, E. D.; de la Cruz, F. N. J. Heterocycl. Chem. 2020, 57, 2279. doi: 10.1002/jhet.v57.5
[16]	Liu, Y. P; Lu, L. X.; Zhou, H. P.; Xu, F. J.; Ma, C.; Huang, Z. J.; Xu, J. Y.; Xu, S. T. RSC Adv. 2019, 9, 34671. doi: 10.1039/C9RA06724H
[17]	Wang, B.-W.; Zhou, Y.-J.; Luo, S.-H.; Luo, X.-Y.; Chen, W.-Q.; Yang, S.-M.; Wang, Z.-Y. Chin. J. Org. Chem. 2021, 41, 171. (in Chinese). doi: 10.6023/cjoc202006064
	( 王柏文, 周永军, 罗时荷, 罗晓燕, 陈伟清, 杨诗敏, 汪朝阳, 有机化学, 2021, 41, 171.)
[18]	Jian, W.-Q.; Wang, H.-B.; Du, K.-S.; Zhong, W.-Q.; Huang, J.-M. ChemElectroChem 2019, 6, 2733. doi: 10.1002/celc.v6.10
[19]	Feng, M.-L.; Li, S.-Q.; He, H.-Z.; Xi, L.-Y.; Chen, S.-Y.; Yu, X.-Q. Green Chem. 2019, 21, 1619. doi: 10.1039/C8GC03622E
[20]	Yang, K.; Yao, C.; Gao, J.-J.; Chen, S.-H.; Zheng, X.-J.; Deng, L.-X.; Zheng, Y.-N.; Liu, M.-J.; Wang, Z.-Y. Chin. J. Org. Chem., 2020, 40, 4168. (in Chinese). doi: 10.6023/cjoc202005074
	( 杨凯, 姚辰, 高娟娟, 陈思鸿, 郑雪洁, 邓璐璇, 张毓娜, 刘美娟, 汪朝阳, 有机化学, 2020, 40, 4168.)
[21]	Cai, Q; Liu, M. C.; Mao, B. M.; Xie, X.; Jia, F. C.; Zhu, Y. P.; Wu, A. X. Chin. Chem. Lett. 2015, 26, 881. doi: 10.1016/j.cclet.2014.12.016
[22]	Meng, X.; Yu, C. Y.; Chen, G. X.; Zhao, P. Q. Catal. Sci. Technol. 2015, 5, 372. doi: 10.1039/C4CY00919C
[23]	Wang, B.-W.; Jiang, K.; Li, J.-X.; Luo, S.-H.; Wang, Z.-Y.; Jiang, H.-F. Angew. Chem., Int. Ed. 2020, 59, 2338. doi: 10.1002/anie.v59.6
[24]	Okai, H.; Tanimoto, K.; Ohkado, R.; Iida, H. Org. Lett. 2020, 22, 8002. doi: 10.1021/acs.orglett.0c02929
[25]	Bhutia, Z. T.; Panjikar, P. C.; Iyer, S.; Chatterjee, A.; Banerjee, M. ACS Omega 2020, 5, 13333. doi: 10.1021/acsomega.0c01478
[26]	Hu, S. P.; Du, S.Y.; Yao, Y. J.; Yang, Z.G.; Ren, H. J.; Chen, Z. K. Synlett 2019, 30, 625. doi: 10.1055/s-0037-1612082
[27]	Haouchine, A. L.; Kabri, Y.; Bakhta, S.; Curti, C. Nedjar-Kolli, B.; Vanelle, P. Synth. Commun. 2018, 48, 2159. doi: 10.1080/00397911.2018.1479759
[28]	Xie, Y. J.; Wu, J.; Che, X. Z.; Chen, Y.; Huang, H. W.; Deng, G.-J. Green Chem. 2016, 18, 667. doi: 10.1039/C5GC01978H
[29]	Nguyen, T. B.; Retailleau, P. Adv. Synth. Catal. 2017, 359, 3843. doi: 10.1002/adsc.v359.21
[30]	Frett, B.; McConnell, N.; Smith, C. C. Wang, Y. X.; Shah, N. P.; Li, H.-Y. Eur. J. Med. Chem. 2015, 94, 123. doi: 10.1016/j.ejmech.2015.02.052
[31]	Tan, J.; Ni, P. H.; Huang, H. W.; Deng, G.-J. Org. Biomol. Chem. 2018, 16, 4227. doi: 10.1039/C8OB00981C
[32]	Zhan, H. Y.; Zhao, L. M.; Liao, J. Q.; Li, N. Y.; Chen, Q. L.; Qiu, S. X.; Cao, H. Adv. Synth. Catal. 2015, 357, 46. doi: 10.1002/adsc.v357.1
[33]	Chen, Z. W.; Liang, P.; Xu, F.; Qiu, R. L.; Tan, Q.; Long, L. P.; Ye, M. J. Org. Chem. 2019, 84, 9369. doi: 10.1021/acs.joc.9b01188
[34]	Wu, H.-Q.; Yang, K.; Chen, X.-Y.; Arulkumar, M.; Wang, N.; Chen, S.-H.; Wang, Z.-Y. Green Chem. 2021, 21, 3782. doi: 10.1039/C9GC01740B
[35]	Bhutia, Z. T.; Das, D.; Chatterjee, A.; Banerjee, M. ACS Omega 2019, 4, 4481. doi: 10.1021/acsomega.8b03581
[36]	Purohit, G.; Kharkwal, A.; Rawat, D. S. ACS Sustainable Chem. Eng. 2020, 8, 5544. doi: 10.1021/acssuschemeng.9b07371
[37]	Rakhtshah, J.; Yaghoobi, F. Int. J. Biol. Macromol. 2019, 139, 904. doi: S0141-8130(19)33804-8 pmid: 31400424
[38]	Ghorbani-Choghamarani, A.; Taherinia, Z. J. Iran. Chem. Soc. 2020, 17, 59. doi: 10.1007/s13738-019-01744-w
[39]	Mala, R.; Suman, K.; Nandhagopal, M.; Narayanasamy, M.; Thennarasu, S. Spectrochim. Acta, Part A 2019, 222, 117236. doi: 10.1016/j.saa.2019.117236
[40]	Soleimani, E.; Torkaman, S.; Sepahvand, H.; Ghorbani, S. Mol. Diversity 2019, 23, 739. doi: 10.1007/s11030-018-9907-3
[41]	Heydari, M.; Azizi, N.; Mirjafari, Z.; Hashemi, M. M. J. Iran. Chem. Soc. 2019, 16, 2357. doi: 10.1007/s13738-019-01705-3
[42]	Sun, J. W.; Yang, X. R.; Liu, Y.; Wang, Y.; Pan, Y. J. Heterocycl. Chem. 2020, 57, 1449. doi: 10.1002/jhet.v57.3
[43]	Zhang, M.; Lu, J.; Zhang, J.-N.; Zhang, Z.-H. Catal. Commun. 2016, 78, 26. doi: 10.1016/j.catcom.2016.02.004
[44]	Xiao, X. S.; Xie, Y.; Bai, S. Y.; Deng, Y. F.; Jiang, H. F.; Zeng, W. Org. Lett. 2015, 17, 3998. doi: 10.1021/acs.orglett.5b01868
[45]	Kumar, S.; Sharma, N.; Maurya, I. K.; Verma, A.; Kumar, S.; Bhasin, K. K.; Sharma, R. K. New J. Chem. 2017, 41, 2919. doi: 10.1039/C7NJ00338B
[46]	Brar, S. K.; Kumar, S.; Pandey, S. K.; Bhasin, K. K.; Wangoo, N.; Sharma, R. K. J. Mol. Liq. 2018, 254, 208. doi: 10.1016/j.molliq.2018.01.090
[47]	Kumar, S.; Sharma, N.; Maurya, I. K.; Bhasin, A. K. K.; Wangoo, N.; Brandao, P.; Felix, V.; Bhasin, K. K.; Sharma, R. K. Eur. J. Med. Chem. 2016, 123, 916. doi: 10.1016/j.ejmech.2016.07.076
[48]	Sarlauskas, J.; Peciukaityte-Alksne, M.; Miseviciene, L.; Maroziene, A.; Polmickaite, E.; Staniulyte, Z.; Cenas, N.; Anusevicius, Z. Bioorg. Med. Chem. Lett. 2026, 26, 512. doi: 10.1016/j.bmcl.2015.11.084
[49]	Karamthulla, S.; Khan, M. N.; Choudhury, L. H. RSC Adv. 2015, 5, 19724. doi: 10.1039/C4RA16298F
[50]	Ramya, P. V. S.; Guntuku, L.; Angapelly, S.; Digwal, C. S.; Lakshmi, U. J.; Sigalapalli, D. K.; Babu, B. N.; Naidu, V. G. M.; Kamal, A. Eur. J. Med. Chem. 2018, 143, 216. doi: S0223-5234(17)30895-4 pmid: 29174816
[51]	Roslan, I. I.; Ng, K. H.; Chuah, G. K.; Jaenicke, S. Adv. Synth. Catal. 2016, 358, 364. doi: 10.1002/adsc.201501012
[52]	Samanta, S. K.; Bera, M. K. Org. Biomol. Chem. 2018, 17, 6441. doi: 10.1039/C9OB00812H
[53]	Rasheed, S.; Rao, D. N.; Das, P. Asian J. Org. Chem. 2016, 5, 1213. doi: 10.1002/ajoc.v5.10
[54]	Cheng, C.; Ge, L.; Lu, X. H.; Huang, J. P.; Huang, H. C.; Chen, J.; Cao, W. G.; Wu, X. Y. Tetrahedron 2016, 72, 6866. doi: 10.1016/j.tet.2016.09.013
[55]	Dheer, D.; Reddy, K. R.; Rath, S. K.; Sangwan, P. L.; Das, P.; Shankar, R. RSC Adv. 2016, 6, 38033. doi: 10.1039/C6RA02953A
[56]	Liu, Y.; Zhang, Y. X.; Sun, J. W. J. Heterocycl. Chem. 2019, 56, 2804. doi: 10.1002/jhet.v56.10
[57]	Tran, R. Q; Jacoby, S. A.; Roberts, K. E.; Swann, W. A.; Harris, N. W.; Dinh, L. P.; Denison, E. L.; Yet, L. RSC Adv. 2019, 9, 17778. doi: 10.1039/C9RA02200G
[58]	Liu, Y.; Wang, W. H.; Han, J. W.; Sun, J. W. Org. Biomol. Chem. 2017, 15, 9311. doi: 10.1039/C7OB02014G
[59]	Li, X. W.; Wang, T. Z.; Lu, Y.-J.; Ji, S. M.; Huo, Y. P.; Liu, B. F. Org. Biomol. Chem. 2018, 16, 7143. doi: 10.1039/C8OB01532E
[60]	Mutkule, N.; Bugad, N.; Mokale, S.; Choudhari, V.; Ubale, M. J. Heterocycl. Chem. 2020, 57, 3186. doi: 10.1002/jhet.v57.8
[61]	Meng, X.; Zhang, J. Q.; Chen, B. H.; Jing, Z. Q.; Zhao, P. Q. Catal. Sci. Technol. 2016, 6, 890. doi: 10.1039/C5CY01433F
[62]	Tzani, M. A.; Kallitsakis, M. G.; Symeonidis, T. S.; Lykakis, I. N. ACS Omega 2018, 3, 17947. doi: 10.1021/acsomega.8b03047
[63]	Nguyen, O. T. K.; Ha, P. T.; Dang, H. V.; Vo, Y. H.; Nguyen, T. T.; Le, N. T. H; Phan, N. T. S. RSC Adv. 2019, 9, 5501. doi: 10.1039/c9ra00097f
[64]	Zhai, L.-H.; Guo, L.-H.; Sun, B.-W. RSC Adv. 2015, 5, 93631. doi: 10.1039/C5RA19085A
[65]	Rao, C. Q.; Mai, S. Y.; Song, Q. L. Org. Lett. 2017, 19, 4726. doi: 10.1021/acs.orglett.7b02015
[66]	Tian, X. H.; Song, L. N.; Wang, M. M.; Lv, Z. G.; Wu, J.; Yu, W. Q.; Chang, J. B. Chem.-Eur. J. 2016, 22, 7617. doi: 10.1002/chem.v22.22
[67]	McDonald, I. M.; Peese, K. M. Org. Lett. 2015, 17, 6002. doi: 10.1021/acs.orglett.5b02966 pmid: 26598965
[68]	Guchhait, S. K.; Saini, M. New J. Chem. 2020, 44, 308. doi: 10.1039/C9NJ04966E
[69]	Verma, K.; Tailor, Y. K.; Khandelwal, S.; Agarwal, M.; Rushell, E.; Kumari, Y.; Awasthi, K.; Kumar, M. RSC Adv. 2018, 8, 30430. doi: 10.1039/C8RA04919J
[70]	Selvi, S.; Srinivasan, K. Eur. J. Org. Chem., 2017, 2017, 5644. doi: 10.1002/ejoc.v2017.37
[71]	Tsoung, J.; Bogdan, A. R.; Kantor, S.; Wang, Y.; Charaschanya, M.; Djuric, S. W. J. Org. Chem. 2017, 82, 1073. doi: 10.1021/acs.joc.6b02520
[72]	Liu, D. Y.; Zhang, J.; Zhao, L.; He, W. J.; Liu, Z. J.; Gan, X. H.; Song, B. A. J. Agric. Food Chem. 2019, 67, 11860. doi: 10.1021/acs.jafc.9b03606
[73]	Roy, A.; Kundu, M.; Dhar, P.; Chakraborty, A.; Mukherjee, S.; Naskar, J.; Rarhi, C.; Barik, R.; Mondal, S. K.; Wani, M. A.; Gajbhiye, R.; Roy, K. K.; Maiti, A.; Manna, P.; Adhikari, S. ChemistrySelect 2020, 5, 4559. doi: 10.1002/slct.v5.15
[74]	Ratni, H.; Ebeling, M.; Baird, J.; Bendels, S.; Bylund, J.; Chen, K. S.; Denk, N.; Feng, Z. H.; Green, L.; Guerard, M.; Jablonski, P.; Jacobsen, B.; Khwaja, O.; Kletzl, H.; Ko, C. P.; Kustermann, S.; Marquet, A.; Metzger, F.; Mueller, B.; Naryshkin, N. A.; Paushkin, S. V.; Pinard, E.; Poirier, A.; Reutlinger, M.; Weetall, M.; Zeller, A.; Zhao, X.; Mueller, L. J. Med. Chem. 2018, 61, 6501. doi: 10.1021/acs.jmedchem.8b00741
[75]	Dong, Z.; Wang, Z.; Guo, Z.-Q.; Gong, S. Z.; Zhang, T.; Liu, J.; Luo, C.; Jiang, H. L.; Yang, C.-G. J. Med. Chem. 2020, 63, 4849. doi: 10.1021/acs.jmedchem.0c00161 pmid: 32297747
[76]	Marshall, A. J.; Lill, C. L.; Chao, M.; Kolekar, S. V.; Lee, W.-J.; Marshall, E. S.; Baguley, B. C.; Shepherd, P. R.; Denny, W. A.; Flanagan, J. U.; Rewcastle, G. W. Bioorg. Med. Chem. 2015, 23, 3796. doi: 10.1016/j.bmc.2015.03.073
[77]	Stepan, A. F.; Claffey, M. M.; Reese, M. R.; Balan, G.; Barreiro, G.; Barricklow, J.; Bohanon, M. J.; Boscoe, B. P.; Cappon, G. D.; Chenard, L. K.; Cianfrogna, J.; Chen, L. G.; Coffman, K. J.; Drozda, S. E.; Dunetz, J. R.; Ghosh, S.; Hou, X. J.; Houle, C.; Karki, K.; Lazzaro, J. T.; Mancuso, J. Y.; Marcek, J. M.; Miller, E. L.; Moen, M. A.; O'Neil, S.; Sakurada, I.; Skaddan, M.; Parikh, V.; Smith, D. L.; Trapa, P.; Tuttle, J. B.; Verhoest, P. R.; Walker, D. P.; Won, A.; Wright, A. S.; Whritenour, J.; Zasadny, K.; Zaleska, M. M.; Zhang, L.; Shaffer, C. L. J. Med. Chem. 2017, 60, 7764. doi: 10.1021/acs.jmedchem.7b00604
[78]	Park, D.-S.; Jo, E.; Choi, J.; Lee, M.; Kim, S.; Kim, H.-Y.; Nam, J.; Ahn, S.; Hwang, J. Y.; Windisch, M. P. Eur. J. Med. Chem. 2017, 140, 65. doi: 10.1016/j.ejmech.2017.09.010
[79]	Jadhav, S. B.; Fatema, S.; Patil, R. B.; Sangshetti, J. N.; Farooqui, M. J. Heterocycl. Chem. 2017, 54, 3299. doi: 10.1002/jhet.v54.6
[80]	Hussain, M.; Liu, J. H. Tetrahedron Lett. 2020, 61, 152269. doi: 10.1016/j.tetlet.2020.152269
[81]	Mathavan, S.; Raj, A. K. D.; Yamajala, R. B. R. D. ChemistrySelect 2019, 4, 10737. doi: 10.1002/slct.v4.36
[82]	Pavithra, T.; Devi, E. S.; Nagarajan, S.; Sridharan, V.; Maheswari, C. U. Eur. J. Org. Chem. 2019, 6884.
[83]	Alanine, T. A.; Galloway, W. R. J. D.; Bartlett, S.; Ciardiello, J. J.; McGuire, T. M.; Spring, D. R. Org. Biomol. Chem. 2015, 14, 1031. doi: 10.1039/C5OB01784J
[84]	Chen, Z. W..; Wen, Y. L.; Ding, H.; Luo, G. T.; Ye, M.; Liu, L. X.; Xue, J. Tetrahedron Lett. 2017, 58, 13. doi: 10.1016/j.tetlet.2016.11.079
[85]	Silpa, L.; Niepceron, A.; Laurent, F.; Brossier, F.; Penichon, M.; Enguehard-Gueiffier, C.; Abarbri, M.; Silvestre, A.; Petrignet, J. Bioorg. Med. Chem. Lett. 2016, 26, 114. doi: 10.1016/j.bmcl.2015.11.018
[86]	Inturi, S. B.; Kalita, B.; Ahamed, A. Synth. Commun. 2018, 48, 2037. doi: 10.1080/00397911.2018.1479761
[87]	Madar, J. M.; Shastri, L. A.; Shastri, S. L.; Holiyachi, M.; Naik, N.; Kulkarni, R.; Shaikh, F.; Sungar, V. Synth. Commun. 2018, 48, 375. doi: 10.1080/00397911.2017.1397698
[88]	Sadeghzadeh, S. M.; Zhiani, R. J. Organomet. Chem. 2018, 868, 47. doi: 10.1016/j.jorganchem.2018.05.002
[89]	Alsharif, Z.; Ali, M. A.; Alkhattabi, H.; Jones, D.; Delancey, E.; Ravikumar, P. C.; Alam, M. A. New J. Chem. 2017, 41, 14862. doi: 10.1039/C7NJ03376A pmid: 29430169
[90]	El-Sayed, R.; Katouah, H. A. J. Heterocycl. Chem. 2019, 56, 2134. doi: 10.1002/jhet.v56.8
[91]	Rao, C. B.; Zhang, N.; Hu, J. N.; Wang, Y.; Liang, Y. J.; Zhang, R.; Yuan, J. W.; Dong, D. W. J. Org. Chem. 2020, 85, 4695. doi: 10.1021/acs.joc.9b03495
[92]	Sagir, H.; Rai, P.; Neha, S.; Singh, P. K.; Tiwari, S.; Siddiqui, I. R. RSC Adv. 2016, 6, 73924. doi: 10.1039/C6RA07085J
[93]	Guchhait, S. K.; Saini, M.; Sumkaria, D.; Chaudhary, V. Chem. Commun. 2017, 53, 6941. doi: 10.1039/C7CC02946B
[94]	Hoang, G. L.; Zoll, A. J.; Ellman, J. A. Org. Lett. 2019, 21, 3886. doi: 10.1021/acs.orglett.9b00779 pmid: 30896175
[95]	Brahmachari, G.; Karmakar, I.; Nurjamal, K. ACS Sustainable Chem. Eng. 2018, 6, 11018. doi: 10.1021/acssuschemeng.8b02448
[96]	Mahdavi, M.; Estabragh, R. F.; Moghimi, S.; Sayahi, M. H.; Shafiee, A.; Foroumadi, A. Synlett 2016, 27, 1359. doi: 10.1055/s-00000083
[97]	Liu, J. D.; Zou, J. H.; Yao, J. W.; Chen, G. S. Adv. Synth. Catal. 2018, 360, 659. doi: 10.1002/adsc.v360.4
[98]	Sha, X.-L.; Niu, J.-Y.; Sun, R.; Xu, Y.-J.; Ge, J.-F. Org. Chem. Front. 2017, 5, 555. doi: 10.1039/C7QO00889A
[99]	Pham, P. H.; Doan, S. H.; Vuong, N. T. H; Nguyen, V. H. H.; Ha, P. T. M.; Phan, N. T. S. RSC Adv. 2018, 8, 20314. doi: 10.1039/C8RA03744B
[100]	Brendel, M.; Sakhare, P. R.; Dahiya, G.; Subramanian, P.; Kaliappan, K. P. J. Org. Chem. 2020, 85, 8102. doi: 10.1021/acs.joc.0c00982
[101]	Feng, J.-B.; Wu, X.-F. Org. Biomol. Chem. 2015, 13, 10656. doi: 10.1039/C5OB01587A
[102]	Xu, T. Y.; Alper, H. Org. Lett. 2015, 17, 1569. doi: 10.1021/acs.orglett.5b00452
[103]	Yuan, Y.; Wu, X.-F. Eur. J. Org. Chem. 2019, 2172.
[104]	Fei, Z. A.; Zhu, Y.-P.; Liu, M.-C.; Jia, F.-C.; Wu, A.-X. Tetrahedron Lett. 2013, 54, 1222. doi: 10.1016/j.tetlet.2012.12.072
[105]	Yang, Y.; Shu, W.-M.; Yu, S.-B.; Ni, F.; Gao, M.; Wu, A.-X. Chem. Commun. 2013, 49, 1729. doi: 10.1039/c3cc38131e
[106]	Li, D.; Wang, Q.; Rao, N.; Zhang, Y.; Le, Y.; Liu, L.; Li, L. L.; Huang, L.; Yan, L. J. J. Mol. Struct. 2021, 1239, 130521. doi: 10.1016/j.molstruc.2021.130521
[107]	Srivastava, S.; Thakur, N.; Singh, A.; Shukla, P.; Maikhuri, V. K.; Garg, N.; Prasad, A.; Pandey, R. RSC Adv. 2019, 9, 29856. doi: 10.1039/c9ra04743c
[108]	Liu, X.; Li, W.; Liu, H. Y.; Cao, H. Chin. J. Org. Chem., 2021, 41, 1759. (in Chinese).
	( 刘想, 李文, 刘环宇, 曹华, 有机化学, 2021, 41, 1759.)