基于2-卤苯甲酰胺合成苯并杂环化合物的研究进展

doi:10.6023/cjoc202101044

有机化学 ›› 2021, Vol. 41 ›› Issue (6): 2175-2187.DOI: 10.6023/cjoc202101044 上一篇下一篇

综述与进展

基于2-卤苯甲酰胺合成苯并杂环化合物的研究进展

杨凯^a^,^b, 刘美娟^a, 张毓娜^a, 占佳琦^a, 邓璐璇^a, 郑雪洁^a, 周永军^a, 汪朝阳^a^,^*()

a 华南师范大学化学学院教育部环境理论化学重点实验室广州市生物医药分析化学重点实验室广州 510006
b 赣南医学院药学院江西赣州 341000

收稿日期:2021-01-26 修回日期:2021-02-20 发布日期:2021-03-04
通讯作者: 汪朝阳
基金资助:
广州市科技计划科学研究专项(201607010251); 广东省科技计划(2017A010103016); 江西省教育厅科学技术研究(GJJ201504); 赣南医学院(YB201903); 广东省大学生创新创业训练计划(S202010574059)

Progress in the Synthesis of Benzoheterocycles from 2-Halobenzamides

Kai Yang^a^,^b, Meijuan Liu^a, Yu'na Zhang^a, Jiaqi Zhan^a, Luxuan Deng^a, Xuejie Zheng^a, Yongjun Zhou^a, Zhaoyang Wang^a()

a Key Laboratory of Theoretical Chemistry of Environment, Ministry of Education, Guangzhou Key Laboratory of Analytical Chemistry for Biomedicine, School of Chemistry, South China Normal University, Guangzhou 510006
b College of Pharmacy, Gannan Medical University, Ganzhou, Jiangxi 341000

Received:2021-01-26 Revised:2021-02-20 Published:2021-03-04
Contact: Zhaoyang Wang
Supported by:
Guangzhou Science and Technology Project Scientific Special(201607010251); Guangdong Provincial Science and Technology Project(2017A010103016); Scientific Research Fund of Jiangxi Provincial Education Department(GJJ201504); Gannan Medical University(YB201903); Undergraduates Innovation Project of Guangdong Province(S202010574059)

文章分享

摘要/Abstract

苯并稠杂环化合物具有广泛且重要的药理及生物活性, 在药物合成与研发领域有着重要的应用价值, 因而其合成方法倍受关注. 由于存在多个官能团和反应位点, 以2-卤代苯甲酰胺为重要合成子合成喹唑啉酮、异喹啉酮、异吲哚酮和苯并异噻唑酮等苯并杂环化合物取得了巨大进展. 鉴于此, 根据产物结构的不同, 概述近10年来以2-卤苯甲酰胺为起始原料合成苯并杂环化合物的研究进展, 并对相关的反应机理进行了阐述.

关键词: 2-卤苯甲酰胺, 金属催化, 串联反应, 环化反应, 苯并杂环化合物, 反应机理

Owing to important pharmacological and biological activities of benzoheterocyclic compounds, their exploration for efficient synthesis methods in drug field is of great value and wide application. Due to the existence of multiple functional groups and reaction sites, great progress has been made in the synthesis of quinazolinones, isoquinolinones, isoindolinones, benzisothiazolones and other benzoheterocyclic compounds using 2-halobenzamides as important synthons. In view of this, according to the different structures of the products, the research progress in the synthesis of benzoheterocyclic compounds with 2-halobenzamides as the starting material in recent 10 years is summarized, and the related reaction mechanism is expounded.

Key words: 2-halobenzamide, metal catalysis, domino reaction, cyclization reaction, benzoheterocyclic compound, reaction mechanism

引用此文

杨凯, 刘美娟, 张毓娜, 占佳琦, 邓璐璇, 郑雪洁, 周永军, 汪朝阳. 基于2-卤苯甲酰胺合成苯并杂环化合物的研究进展[J]. 有机化学, 2021, 41(6): 2175-2187.

Kai Yang, Meijuan Liu, Yu'na Zhang, Jiaqi Zhan, Luxuan Deng, Xuejie Zheng, Yongjun Zhou, Zhaoyang Wang. Progress in the Synthesis of Benzoheterocycles from 2-Halobenzamides[J]. Chinese Journal of Organic Chemistry, 2021, 41(6): 2175-2187.

导出引用 EndNote|Reference Manager|ProCite|BibTeX|RefWorks

分享此文

图/表 16

图1. 具有苯并杂环化合物的天然产物及药物分子

Figure 1. Natural products and drug molecules with benzoheterocyclic compounds

图式1. 2-卤苯甲酰胺合成喹唑啉酮分子的逆合成分析

Scheme 1. Retrosynthetic analysis for the synthesis of quinazolinones from 2-halobenzamides

图式2. 铜催化合成喹唑啉酮类化合物

Scheme 2. Copper catalyzed synthesis of quinazolinone derivatives

图式3. 2-卤苯甲酰胺和苄胺合成2-芳基喹唑啉酮

Scheme 3. 2-Arylquinazolinones were synthesized from 2-halobenzamides and benzylamines

图式4. 2-卤苯甲酰胺和α-氨基酸合成喹唑啉酮

Scheme 4. Synthesis of quinazolinones from 2-halobenzamides and α-amino acids

图式5. 2-卤苯甲酰胺和烯胺酮合成喹唑啉酮

Scheme 5. Synthesis of quinazolinones from 2-halobenzamides and enaminones

图式6. 2-卤苯甲酰胺和酰胺合成喹唑啉酮

Scheme 6. Synthesis of quinazolinones from 2-halobenzamides and amides

图式7. 2-卤苯甲酰胺和叠氮化钠合成喹唑啉酮

Scheme 7. Synthesis of quinazolinones from 2-halobenzamides and sodium azide

图式8. 2-卤苯甲酰胺合成异喹啉酮类分子的逆合成分析

Scheme 8. Retrosynthetic analysis for the synthesis of isoquinolinones from 2-halobenzamides

图式9. Ni催化2-氟甲酰胺与炔的反应机理

Scheme 9. Reaction mechanism of Ni catalyzed 2-fluoro- benzamides with alkynes

图式10. 钯催化邻卤苯甲酰胺合成菲啶酮

Scheme 10. Palladium-catalyzed synthesis of phenanthridinones from o-halobenzamides

图式11. 钯催化邻溴苯甲酰胺的偶联反应

Scheme 11. Pd-Catalyzed coupling of o-bromobenzamides

图式12. CuI/L-脯氨酸催化的2-溴苯甲酰胺和末端炔烃的串联反应

Scheme 12. CuI/L-proline catalyzed domino reaction of 2-bromobenzamide and terminal alkynes

图式13. 苯并异硒(噻)唑酮的制备

Scheme 13. Preparation of benzoisothiazolones

图式14. 2-溴苯甲酰胺和硫氰酸钾合成苯并异噻唑-3(2H)-酮

Scheme 14. Synthesis of benzisoselenazole-3(2H)-ones from 2-bromobenzoamides and potassium thiocyanate

图式15. 二苯并噁氮杂蒎酮的合成

Scheme 15. Synthesis of dibenzoxazepinones

参考文献 109

[1]	Stepien, M.; Gonka, E.; Zyla, M.; Sprutta, N. Chem. Rev. 2017, 117,3479. doi: 10.1021/acs.chemrev.6b00076
[2]	Zhang, X.-P.; Zhu, Y.-J.; Zhu, Y.-S.; Li, Z.-W.; Zhang, G.-S. Chin. J. Org. Chem. 2019, 39,2392(in Chinese). doi: 10.6023/cjoc201903025
	( 张晓鹏, 朱妍洁, 朱奕崧, 李政伟, 张贵生, 有机化学, 2019, 39,2392.) doi: 10.6023/cjoc201903025
[3]	(a) Doncheva, T.; Solongo, A.; Kostova, N.; Gerelt-Od, Y.; Selenge, D.; Philipov, S. Nat. Prod. Res. 2015, 29,853. doi: 10.1080/14786419.2014.991322
	(b) Yu, X.-Y.; Zhou, F.; Chen, J.-R.; Xiao, W.-J. Acta Chim. Sinica 2017, 75,86(in Chinese). doi: 10.6023/A16070367
	( 余晓叶, 周帆, 陈加荣, 肖文精, 化学学报, 2017, 75,86.)
[4]	(a) Yao, T.-L.; Guo, Z.; Liang, X.-J.; Qi, L.-H. J. Org. Chem. 2018, 83,13370. doi: 10.1021/acs.joc.8b02154
	(b) Zhang, L.-B.; Wang, Z.-C.; Sun, S.-Z.; Ni, S.-F.; Wen, L.-R.; Li, M. Chin. J. Chem. 2021, 39,903. doi: 10.1002/cjoc.v39.4
[5]	Novick, R. M.; Nelson, M. L.; Unice, K. M.; Keenan, J. J.; Paustenbach, D. J. Food Chem. Toxicol. 2013, 56,60. doi: 10.1016/j.fct.2013.02.006
[6]	Bu, X.-L.; He, B.-B.; Weng, J.-Y.; Jiang, C.-C.; Zhao, Y.-L.; Li, S.-M.; Xu, J.; Xu, M.-J. ACS Synth. Biol. 2020, 9,2282. doi: 10.1021/acssynbio.9b00405 pmid: 32786357
[7]	(a) Zhou, L.-J.; Li, S.-L.; Xu, B.; Ji, D.-T.; Wu, L.-Z.; Liu, Y.; Zhang, Z.-M.; Zhang, J.-L. Angew.Chem., Int. Ed. 2020, 59,2769.
	(b) Li, J.-X.; Xue, F.-L.; Tan, Y.-H.; Luo, S.-H.; Wang, Z.-Y. Acta Chim. Sinica 2011, 69,1688(in Chinese).
	( 李建晓, 薛福玲, 谭越河, 罗时荷, 汪朝阳, 化学学报, 2011, 69,1688.)
[8]	(a) Yang, K.; Qiu, Y.-T.; Li, Z.; Wang, Z.-Y.; Jiang, S. J. Org. Chem. 2011, 76,3151. doi: 10.1021/jo1026035 pmid: 21786767
	(b) Yang, K.; Li, Z.; Wang, Z.-Y.; Yao, Z.-Y.; Jiang, S. Org. Lett. 2011, 13,4340. doi: 10.1021/ol2016737 pmid: 21786767
	(c) Marina, N.; Lanterna, A. E.; Scaiano, J. C. ACS Catal. 2018, 8,7593. doi: 10.1021/acscatal.8b02026 pmid: 21786767
[9]	Dorel, R.; Grugel, C. P.; Haydl, A. M. Angew. Chem., Int. Ed. 2019, 58,17118. doi: 10.1002/anie.v58.48
[10]	(a) Zhao, H.-B.; Fu, H.; Qiao, R.-Z. J. Org. Chem. 2010, 75,3311. doi: 10.1021/jo100345t
	(b) Kadu, R.; Batabyal, M.; Kadyan, H.; Koner, A. L.; Kumar, S. Dalton Trans. 2019, 48,7249. doi: 10.1039/C8DT04832K
	(c) Li, J.-X.; Wang, Z.-Y.; Xue, F.-L.; Luo, S.-H. Acta Chim. Sinica 2011, 69,2835(in Chinese).
	( 李建晓, 汪朝阳, 薛福玲, 罗时荷, 化学学报, 2011, 69,2835.)
[11]	(a) Xu, Y.-M.; Chen, X.-Q.; Gao, Y.-Q.; Yan, Z.-C.; Wan, C.-F.; Liu, J.-B.; Wang, Z.-Y. J. Org. Chem. 2020, 85,4354. doi: 10.1021/acs.joc.0c00048
	(b) Liu, Y.-X.; Xu, W.-Q.; Wang, X. Org. Lett. 2020, 12,1448. doi: 10.1021/ol100153h
[12]	(a) 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.) doi: 10.6023/cjoc202005074
	(b) Sun, J.; Cao, J.; Han, Y.; Yan, C.-G. Chin. J. Org. Chem. 2020, 40,4122(in Chinese). doi: 10.6023/cjoc202005003
	( 孙晶, 曹鋆, 韩莹, 颜朝国, 有机化学, 2020, 40,4122.) doi: 10.6023/cjoc202005003
	(c) Guo, W.; Zhao, M.-M.; Tan, W.; Zheng, L.-Y.; Tao, K.-L.; Fan, X.-L. Org. Chem. Front. 2019, 6,2120. doi: 10.1039/C9QO00283A
	(d) Chen, X.; Bai, L.-L.; Zeng, W. Chin. J. Org. Chem. 2018, 38,1859(in Chinese). doi: 10.6023/cjoc201804033
	( 陈训, 白丽丽, 曾伟, 有机化学, 2018, 38,1859.) doi: 10.6023/cjoc201804033
[13]	(a) Balakumar, C.; Lamba, P.; Pran Kishore, D.; Lakshmi Narayana, B.; Venkat Rao, K.; Rajwinder, K.; Raghuram Rao, A.; Shireesha, B.; Narsaiah, B. Eur. J. Med. Chem. 2010, 45,4904. doi: 10.1016/j.ejmech.2010.07.063 pmid: 25629446
	(b) Bouley, R.; Kumarasiri, M.; Peng, Z. H.; Otero, L. H.; Song, W.; Suckow, M. A.; Schroeder, V. A.; Wolter, W. R.; Lastochkin, E.; Antunes, N. T.; Pi, H. L.; Vakulenko, S.; Hermoso, J. A.; Chang, M.; Mobashery, S. J. Am. Chem. Soc. 2015, 137,1738. doi: 10.1021/jacs.5b00056 pmid: 25629446
[14]	Xu, W.; Jin, Y.-B.; Liu, H.-X.; Jiang, Y.-Y.; Fu, H. Org. Lett. 2011, 13,1274. doi: 10.1021/ol1030266
[15]	Kotipalli, T.; Kavala, V.; Janreddy, D.; Bandi, V.; Kuo, C.-W.; Yao, C.-F. Eur. J. Org. Chem. 2016, 2016 1182.
[16]	Modi, A.; Ali, W.; Mohanta, P. R.; Khatun, N.; Patel, B. K. ACS Sustainable Chem. Eng. 2015, 3,2582. doi: 10.1021/acssuschemeng.5b00817
[17]	Yan, N.; You, C.-R.; Cai, M.-Z. J. Organomet. Chem. 2019, 897,161. doi: 10.1016/j.jorganchem.2019.07.003
[18]	Sharma, R.; Vishwakarma, R. A.; Bharate, S. B. Adv. Synth. Catal. 2016, 358,3027. doi: 10.1002/adsc.v358.19
[19]	Wang, L.-X.; Xiang, J.-F.; Tang, Y.-L. Eur. J. Org. Chem. 2014, 2014 ,2682. doi: 10.1002/ejoc.v2014.13
[20]	Hu, B.-Q.; Wang, L.-X.; Xiang, J.-F.; Yang, L.; Tang, Y.-L. Chin. Chem. Lett. 2015, 26,369. doi: 10.1016/j.cclet.2014.12.006
[21]	Xu, W.; Fu, H. J. Org. Chem. 2011, 76,3846. doi: 10.1021/jo2002227
[22]	Kong, L.-L.; Fan, L.-Y. Chin. Chem. Lett. 2016, 27,827. doi: 10.1016/j.cclet.2016.01.055
[23]	Nazarenko, K. G.; Shyrokaya, T. I.; Tolmachev, A. A. Synth. Commun. 2003, 33,303. doi: 10.1081/SCC-120015716
[24]	Zhou, J.; Fu, L.-B.; Lv, M.; Liu, J.-S.; Pei, D.-Q.; Ding, K. Synthesis 2008,3974.
[25]	Songsichan, T.; Promsuk, J.; Rukachaisirikul, V.; Kaeobamrung, J. Org. Biomol. Chem. 2014, 12,4571. doi: 10.1039/c4ob00400k pmid: 24860848
[26]	Tian, H.; Qiao, H.-W.; Zhu, C.-J.; Fu, H. RSC Adv. 2014, 4,2694. doi: 10.1039/C3RA44975K
[27]	Xu, L.-T.; Jiang, Y.-W.; Ma, D.-W. Org. Lett. 2012, 14,1150. doi: 10.1021/ol300084v
[28]	Kumar, A.; Bishnoi, A. K. RSC Adv. 2014, 4,41631. doi: 10.1039/C4RA06804A
[29]	Iqbal, M. A.; Lu, L.; Mehmood, H.; Khan, D. M.; Hua, R. M. ACS Omega 2019, 4,8207. doi: 10.1021/acsomega.9b00699
[30]	Sayyad, N.; Cele, Z.; Aleti, R. R.; Bera, M.; Cherukupalli, S.; Chandrasekaran, B.; Kushwaha, N. D.; Karpoormath, R. Eur. J. Org. Chem. 2018, 2018 5382.
[31]	Yu, X.-Q.; Gao, L.-Q.; Jia, L.-A.; Yamamoto, Y.; Bao, M. J. Org. Chem. 2018, 83,10352. doi: 10.1021/acs.joc.8b01460
[32]	Wang, F.; Zhao, P.; Xi, C.-J. Tetrahedron Lett. 2011, 52,231. doi: 10.1016/j.tetlet.2010.11.010
[33]	Yang, K.; Yang, J.-Q.; Luo, S.-H.; Mei, W.-J.; Lin, J.-Y.; Zhan, J.-Q.; Wang, Z.-Y. Bioorg. Chem. 2021, 107,104518. doi: 10.1016/j.bioorg.2020.104518
[34]	Krishna, M. H.; Thriveni, P. Heterocycl. Lett. 2018, 8,229.
[35]	Liu, Z.-B.; Zeng, L.-Y.; Li, C.; Yang, F.-B.; Qiu, F.-S.; Liu, S.-W.; Xi, B.-M. Molecules 2018, 23,2325. doi: 10.3390/molecules23092325
[36]	Guo, S.-H.; Li, Y.; Tao, L.; Zhang, W.-W.; Fan, X.-S. RSC Adv. 2014, 4,59289. doi: 10.1039/C4RA10799C
[37]	Upadhyaya, K.; Thakur, R. K.; Shukla, S. K.; Tripathi, R. P. J. Org. Chem. 2016, 81,5046. doi: 10.1021/acs.joc.6b00599
[38]	Li, T.; Chen, M.-L.; Yang, L.; Xiang, Z.-X.; Wang, Y.-W.; Li, F.; Chen, D.-Y. Tetrahedron 2016, 72,868. doi: 10.1016/j.tet.2015.12.059
[39]	Shinde, M. H.; Kshirsagar, U. A. RSC Adv. 2016, 6,52884. doi: 10.1039/C6RA10997G
[40]	Nandwana, N. K.; Dhiman, S.; Saini, H. K.; Kumar, I.; Kumar, A. Eur. J. Org. Chem. 2017, 2017 514.
[41]	Dao, P.-D.-Q.; Cho, C.-S.; Ho, S.-L.; Sohn, H.-S. Curr. Org. Chem. 2018, 22,85. doi: 10.2174/1385272821666170531122318
[42]	Xu, H.; Fu, H. Chem.-Eur. J., 2012, 18,1180. doi: 10.1002/chem.201102794
[43]	Abe, T.; Takahashi, Y.; Matsubara, Y.; Yamada, K. Org. Chem. Front. 2017, 4,2124. doi: 10.1039/C7QO00549K
[44]	Upadhyay, N. S.; Thorat, V. H.; Sato, R.; Annamalai, P.; Chuang, S. C.; Cheng, C. H. Green Chem. 2017, 19,3219. doi: 10.1039/C7GC01221G
[45]	Weng, W.-Z.; Xie, J.; Zhang, B. Org. Biomol. Chem. 2018, 16,3983. doi: 10.1039/C8OB00795K
[46]	Liu, C.-C.; Parthasarathy, K.; Cheng, C.-H. Org. Lett. 2010, 12,3518. doi: 10.1021/ol101371c
[47]	Nohira, I.; Liu, S.; Bai, R.; Lan, Y.; Chatani, N. J. Am. Chem. Soc. 2020, 142,17306. doi: 10.1021/jacs.0c08512
[48]	de Salinas, S. M.; Sanjose-Orduna, J.; Odena, C.; Barranco, S.; Benet-Buchholz, J.; Perez-Temprano, M. H. Angew. Chem., Int. Ed. 2020, 59,6239. doi: 10.1002/anie.v59.15
[49]	Chary, R. G.; Dhananjaya, G.; Prasad, K. V.; Vaishaly, S.; Ganesh, Y. S. S.; Dulla, B.; Kumar, K. S.; Pal, M. Chem. Commun. 2014, 50,6797. doi: 10.1039/c4cc01580k
[50]	Zhao, H.; Wu, Y.-C.; Wei, T.; Cai, M.-Z. J. Chem. Res. 2014,634.
[51]	Wang, F.; Liu, H.-X.; Fu, H.; Jiang, Y.-Y.; Zhao, Y.-F. Org. Lett. 2009, 11,2469. doi: 10.1021/ol900847t
[52]	Huang, C.-Y.; Kavala, V.; Kuo, C.-W.; Konala, A.; Yang, T.-H.; Yao, C.-F. J. Org. Chem. 2017, 82,1961. doi: 10.1021/acs.joc.6b02814
[53]	Shi, Y.; Zhu, X.-B.; Mao, H.-B.; Hu, H.-W.; Zhu, C.-J.; Cheng, Y.-X. Chem.-Eur. J. 2013, 19,11553. doi: 10.1002/chem.v19.35
[54]	Guastavino, J. F.; Barolo, S. M.; Rossi, R. A. Eur. J. Org. Chem. 2006, 2006 3898.
[55]	Gong, X.-Q.; Li, G.-Q.; Gan, Z.-Y.; Yan, Q.-L.; Dou, X.-M.; Yang, D.-S. Asian J. Org. Chem. 2019, 8,1472. doi: 10.1002/ajoc.v8.8
[56]	Liu, Y.-Y.; Zeng, R.-S.; Pan, J.; Zou, J.-P. Chin. J. Chem. 2014, 32,883. doi: 10.1002/cjoc.201400237
[57]	Lu, J.-Y.; Gong, X.-Y.; Yang, H.-J.; Fu, H. Chem. Commun. 2010, 46,4172. doi: 10.1039/c0cc00185f
[58]	Liu, T.; Wang, R.-J.; Yang, H.-J.; Fu, H. Chem.-Eur. J., 2011, 17,6765. doi: 10.1002/chem.v17.24
[59]	Kavala, V.; Yang, Z.-H.; Konala, A.; Huang, C.-Y.; Kuo, C.-W.; Yao, C.-F. J. Org. Chem. 2017, 82,7280. doi: 10.1021/acs.joc.7b00862
[60]	Cong, W.; Xu, J.-Y.; Yao, H.-Q. Chin. J. Org. Chem. 2014, 34,1966. doi: 10.6023/cjoc201404041
	( 丛蔚, 徐进宜, 姚和权, 有机化学, 2014, 34,1966.) doi: 10.6023/cjoc201404041
[61]	Dao, P. D. Q.; Lim, H. J.; Cho, C. S. ACS Omega 2018, 3,12114. doi: 10.1021/acsomega.8b01742
[62]	Ferraccioli, R.; Carenzi, D.; Rombola, O.; Catellani, M. Org. Lett. 2004, 6,4759. pmid: 15575679
[63]	Yadav, L.; Tiwari, M. K.; Shyamlal, B. R. K.; Chaudhary, S. J. Org. Chem. 2020, 85,8121. doi: 10.1021/acs.joc.0c01019
[64]	Bhakuni, B. S.; Kumar, A.; Balkrishna, S. J.; Sheikh, J. A.; Konar, S.; Kumar, S. Org. Lett. 2012, 14,2838. doi: 10.1021/ol301077y pmid: 22621204
[65]	Nishiyama, Y.; Nakamura, M.; Misawa, T.; Nakagomi, M.; Makishima, M.; Ishikawa, M.; Hashimoto, Y. Bioorg. Med. Chem. 2014, 22,2799. doi: 10.1016/j.bmc.2014.03.007
[66]	Hu, Q.-F.; Gao, T.-T.; Shi, Y.-J.; Lei, Q.; Yu, L.-T. RSC Adv. 2018, 8,13879. doi: 10.1039/C8RA02099J
[67]	Furuta, T.; Kitamura, Y.; Hashimoto, A.; Fujii, S.; Tanaka, K.; Kan, T. Org. Lett. 2007, 9,183. doi: 10.1021/ol062599z
[68]	Liu, H.-L.; Han, W.-B.; Li, C.; Ma, Z.-Y.; Li, R.-X.; Zheng, X.-L.; Fu, H.-Y.; Chen, H. Eur. J. Org. Chem. 2016, 2016 389.
[69]	Chen, X.-W.; Liu, Y.-Y. ChemistrySelect 2018, 3,7763. doi: 10.1002/slct.v3.27
[70]	Donati, L.; Leproux, P.; Prost, E.; Michel, S.; Tillequin, F.; Gandon, V.; Poree, F. H. Chem.-Eur. J. 2011, 17,12809. doi: 10.1002/chem.201101354
[71]	Chavan, S. P.; Bhanage, B. M. Eur. J. Org. Chem. 2015, 2015 2405.
[72]	Wang, Y.-Y.; Zhou, Y.; Lei, M.; Hou, J.-J.; Jin, Q.-H.; Guo, D.; Wu, W.-Y. Tetrahedron 2019, 75,1180. doi: 10.1016/j.tet.2019.01.023
[73]	De, R. P.; Bera, M. K. Synth. Commun. 2020, 50,1780. doi: 10.1080/00397911.2020.1753776
[74]	Sarkar, S.; Dutta, S.; Dey, R.; Naskar, S. Tetrahedron Lett. 2012, 53,6789. doi: 10.1016/j.tetlet.2012.10.001
[75]	Peytam, F.; Adib, M.; Mahernia, S.; Rahmanian-Jazi, M.; Jahani, M.; Masoudi, B.; Mandavi, M.; Amanlou, M. Bioorg. Chem. 2019, 87,1. doi: 10.1016/j.bioorg.2019.02.051
[76]	Yang, P.; You, S.-L. Org. Lett. 2018, 20,7684. doi: 10.1021/acs.orglett.8b03425
[77]	Li, L.; Wang, M.; Zhang, X.-J.; Jiang, Y.-W.; Ma, D.-W. Org. Lett. 2009, 11,1309. doi: 10.1021/ol9000922 pmid: 19226134
[78]	Pan, J.; Xu, Z.; Zeng, R.-S.; Zou, J.-P. Chin. J. Chem. 2013, 31,1022. doi: 10.1002/cjoc.v31.8
[79]	Zhang, L.; Zhang, Y.-L.; Wang, X.; Shen, J.-K. Molecules 2013, 18,654. doi: 10.3390/molecules18010654 pmid: 23292328
[80]	Hazarika, D.; Phukan, P. ChemistrySelect 2018, 3,2474. doi: 10.1002/slct.201702875
[81]	Munoz, S. B.; Aloia, A. N.; Moore, A. K.; Papp, A.; Mathew, T.; Fustero, S.; Olah, G. A.; Prakash, G. K. S. Org. Biomol. Chem. 2016, 14,85. doi: 10.1039/C5OB02187A
[82]	Gogoi, A.; Guin, S.; Rout, S. K.; Majji, G.; Patel, B. K. RSC Adv. 2014, 4,59902. doi: 10.1039/C4RA12782J
[83]	Sarkar, S.; Chatterjee, N.; Roy, M.; Pal, R.; Sarkar, S.; Sen, A. K. RSC Adv. 2014, 4,7024. doi: 10.1039/c3ra46168h
[84]	Sarkar, S.; Pal, R.; Sen, A. K. Tetrahedron Lett. 2013, 54,4273. doi: 10.1016/j.tetlet.2013.05.151
[85]	Chatterjee, N.; Sarkar, S.; Pal, R.; Sen, A. K. Tetrahedron Lett. 2013, 54,3748. doi: 10.1016/j.tetlet.2013.05.004
[86]	Hellal, M.; Cuny, G. D. Tetrahedron Lett. 2011, 52,5508. doi: 10.1016/j.tetlet.2011.08.070
[87]	Xiong, J.; Zhong, G.-F.; Liu, Y.-Y. Adv. Synth. Catal. 2019, 361,550. doi: 10.1002/adsc.201801221
[88]	Pacula, A. J.; Kaczor, K. B.; Wojtowicz, A.; Antosiewicz, J.; Janecka, A.; Dlugosz, A.; Janecki, T.; Scianowski, J. Bioorg. Med. Chem. 2017, 25,126. doi: 10.1016/j.bmc.2016.10.018
[89]	Li, T.; Yang, L.; Ni, K.-D.; Shi, Z.-Y.; Li, F.; Chen, D.-Y. Org. Biomol. Chem. 2016, 14,6297. doi: 10.1039/C6OB00819D
[90]	Cao, L.; Luo, S.-H.; Wu, H.-Q.; Chen, L.-Q.; Jiang, K.; Hao, Z.-F.; Wang, Z.-Y. Adv. Synth. Catal. 2017, 359,2961. doi: 10.1002/adsc.v359.17
[91]	Krasikova, V.; Katkevics, M. Chem. Heterocycl. Compd. 2013, 48,1684. doi: 10.1007/s10593-013-1193-5
[92]	Balkrishna, S. J.; Bhakuni, B. S.; Chopra, D.; Kumar, S. Org. Lett. 2010, 12,5394. doi: 10.1021/ol102027j pmid: 21053969
[93]	Bhakuni, B. S.; Balkrishna, S. J.; Kumar, A.; Kumar, S. Tetrahedron Lett. 2012, 53,1354. doi: 10.1016/j.tetlet.2012.01.003
[94]	Pacula, A. J.; Scianowski, J.; Aleksandrzak, K. B. RSC Adv. 2014, 4,48959. doi: 10.1039/C4RA08631G
[95]	Wu, H.-Q.; Yang, K.; Luo, S.-H.; Wu, X.-Y.; Wang, N.; Chen, S.-H.; Wang, Z.-Y. Eur. J. Org. Chem. 2019, 2019 4572.
[96]	Wu, H.-Q.; Yang, K.; Chen, X.-Y.; Mani, A.; Wang, N.; Chen, S.-H.; Wang, Z.-Y. Green Chem. 2019, 21,3782. doi: 10.1039/C9GC01740B
[97]	Wang, F.; Chen, C.; Deng, G.; Xi, C.-J. J. Org. Chem, 2012, 77,4148. doi: 10.1021/jo300250x
[98]	Thanna, S.; Goins, C. M.; Knudson, S. E.; Slayden, R. A.; Ronning, D. R.; Sucheck, S. J. J. Org. Chem. 2017, 82,3844. doi: 10.1021/acs.joc.7b00440
[99]	Chen, X.-W.; Hao, W.-Y.; Liu, Y.-Y. Org. Biomol. Chem. 2017, 15,3423. doi: 10.1039/C7OB00625J
[100]	Cai, S.-J.; Wang, F.; Xi, C.-J. Synthesis 2012, 44,1892. doi: 10.1055/s-0031-1290949
[101]	Wang, X.-W.; Wu, C.-L.; Sun, Y.-W.; Yao, X.-Q. Tetrahedron Lett. 2017, 58,3164. doi: 10.1016/j.tetlet.2017.07.001
[102]	Kavala, V.; Wang, C.-C.; Barange, D. K.; Kuo, C.-W.; Lei, P.-M.; Yao, C.-F. J. Org. Chem. 2012, 77,5022. doi: 10.1021/jo300501j
[103]	Chen, Q.; Wang, Y.-P.; Hua, R.-M. Molecule 2019, 24, 3773.
[104]	Gawande, S. D.; Kavala, V.; Zanwar, M. R.; Kuo, C.-W.; Huang, W.-C.; Kuo, T.-S.; Huang, H. N.; He, C. H.; Yao, C. F. Adv. Synth. Catal. 2014, 356,2599. doi: 10.1002/adsc.v356.11/12
[105]	Chen, Y.-Y.; Peng, Q.-J.; Zhang, R.; Hu, J.; Zhou, Y.-J.; Xu, L.-T.; Pan, X.-H. Synlett 2017, 28,1201. doi: 10.1055/s-0036-1558959
[106]	Liu, S.-H.; Hu, Y.; Qian, P.-F.; Hu, Y.-W.; Ao, G.-Z.; Chen, S.-H.; Zhang, S.-L.; Zhang, Y.-N. Tetrahedron Lett. 2015, 56,2211.
[107]	Kitching, M. O.; Hurst, T. E.; Snieckus, V. Angew. Chem., Int. Ed. 2012, 51,2925. doi: 10.1002/anie.201106786
[108]	Zhou, W.-J.; Jiang, Y.-X.; Chen, L.; Liu, K.-X.; Yu, D.-G. Chin. J. Org. Chem. 2020, 40,3697(in Chinese). doi: 10.6023/cjoc202004045
	( 周文俊, 蒋元旭, 陈亮, 刘开兴, 余达刚, 有机化学, 2020, 40,3697.) doi: 10.6023/cjoc202004045
[109]	Waldvogel, S. R.; Lips, S.; Selt, M.; Riehl, B.; Kampf, C. J. Chem. Rev. 2018, 118,6706. doi: 10.1021/acs.chemrev.8b00233

基于2-卤苯甲酰胺合成苯并杂环化合物的研究进展

Progress in the Synthesis of Benzoheterocycles from 2-Halobenzamides

RichHTML

PDF

可视化

摘要/Abstract

引用此文

分享此文

图/表 16

参考文献 109

相关文章 15

编辑推荐

相关统计

本文评价

[1]	赵茜帆, 陈永正, 张世明. 碳基非金属催化剂在有机合成领域的应用及机理研究[J]. 有机化学, 2024, 44(1): 137-147.
[2]	赵红琼, 于淼, 宋冬雪, 贾琦, 刘颖杰, 季宇彬, 许颖. 羧酸脱羧羟基化反应研究进展[J]. 有机化学, 2024, 44(1): 70-84.
[3]	高晓阳, 翟锐锐, 陈训, 王烁今. 碳酸亚乙烯酯参与C—H键活化反应的研究进展[J]. 有机化学, 2023, 43(9): 3119-3134.
[4]	张素珍, 张文文, 杨慧, 顾庆, 游书力. 铑催化2-烯基苯酚与炔烃的对映体选择性螺环化反应[J]. 有机化学, 2023, 43(8): 2926-2933.
[5]	陈新强, 张敬. 伯醇的脱羟甲基反应的研究进展[J]. 有机化学, 2023, 43(8): 2711-2719.
[6]	陈玉琢, 孙红梅, 王亮, 胡方芝, 李帅帅. 基于α-氢迁移策略构建杂环骨架的研究进展[J]. 有机化学, 2023, 43(7): 2323-2337.
[7]	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.
[8]	孙李星, 孙婷婷, 王海清, 吴淑芳, 王小烨, 刘天雅, 张宇辰. Lewis酸催化下3-烷基-2-吲哚烯与α,β-不饱和N-磺酰基亚胺的[2+4]环化反应[J]. 有机化学, 2023, 43(6): 2178-2188.
[9]	任志军, 罗维纬, 周俊. 银介导的N-芳基丙烯酰胺串联环化反应研究进展[J]. 有机化学, 2023, 43(6): 2026-2039.
[10]	徐光利, 许静, 徐海东, 崔香, 舒兴中. 过渡金属催化烯烃和炔烃合成1,3-共轭二烯化合物研究进展[J]. 有机化学, 2023, 43(6): 1899-1933.
[11]	莫百川, 陈春霞, 彭进松. 木质素及其衍生物负载金属催化剂在有机合成中的应用研究进展[J]. 有机化学, 2023, 43(4): 1215-1240.
[12]	李靖鹏, 黄顺桃, 杨棋, 李伟强, 刘腾, 黄超. 利用连续流动技术合成(Z)-N-乙烯基取代N,O-缩醛[J]. 有机化学, 2023, 43(4): 1550-1558.
[13]	南江, 黄冠杰, 胡岩, 王波. 钌催化喹唑啉酮与碳酸亚乙烯酯的C—H [4＋2]环化反应[J]. 有机化学, 2023, 43(4): 1537-1549.
[14]	庞明杨, 常宏宏, 冯璋, 张娟. 过渡金属催化吲哚的串联去芳构化反应研究进展[J]. 有机化学, 2023, 43(4): 1271-1291.
[15]	纪健, 刘进华, 管丛, 陈绪文, 赵芸, 刘顺英. 原位生成的磺酸催化N-磺酰基-1,2,3-三氮唑与醇偶联高区域选择性合成N²-取代1,2,3-三氮唑[J]. 有机化学, 2023, 43(3): 1168-1176.