卤素盐参与下有机电合成含氮杂环化合物的研究进展

doi:10.6023/cjoc202007049

摘要/Abstract

含氮杂环化合物广泛存在于医药、农药及天然产物中, 是许多具有生理活性的化合物和药物的基本骨架. 开发高效、绿色的含氮杂环化合物的构建方法具有重要意义. 近年来, 卤素盐参与下有机电合成含氮杂环化合物取得了诸多进展. 该类反应具有操作简单、绿色环保等特点. 综述了有机电化学合成反应中, 卤素盐作媒介, 含氮杂环化合物的合成研究新进展.

关键词: 卤素盐, 电化学合成, 含氮杂环

Nitrogenous heterocyclic compounds are widely found in medicinal molecules, natural products and functional materials. Therefore, it has great significance to develop simple and efficient methods for the construction of these compounds. Recently, remarkable progress has been made in haloids mediated electrochemical synthesis of nitrogen heterocycles. Due to the relatively mild reaction condition and environmental protection, it provides a novel approach to construct nitrogen heterocycles. In this review, the recent developments in this area are summarized.

Key words: haloids, electrochemical synthesis, nitrogenous heterocyclic compounds

引用此文

周娅琴, 赵志恒, 曾亮, 李鸣, 何永辉, 谷利军. 卤素盐参与下有机电合成含氮杂环化合物的研究进展[J]. 有机化学, 2021, 41(3): 1072-1080.

Yaqin Zhou, Zhiheng Zhao, Liang Zeng, Ming Li, Yonghui He, Lijun Gu. Recent Advance in Organic Electrochemical Synthesis of Nitrogenous Heterocyclic Compounds Involving Haloids as Mediators[J]. Chinese Journal of Organic Chemistry, 2021, 41(3): 1072-1080.

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图/表 24

图式1. 碘盐为媒介电化学催化合成吖丙啶的可能机理

Scheme 1. Proposed reaction mechanism for electro-catalyzed synthesis of aziridines mediated by iodized salt

图式2. 电化学催化β-氨基酮合成吖丙啶衍生物

Scheme 2. Electrochemical synthesis of aziridines from β-amino ketones

图式3. 电化学催化合成噁二唑化合物

Scheme 3. Electrosynthesis of oxadiazoles

图式4. 电化学催化合成1,2,4-噻二唑

Scheme 4. Electrochemical synthesis of 1,2,4-thiadiazoles

图式5. 电化学催化合成1,2,3-噻二唑的可能机理

Scheme 5. Proposed reaction mechanism for electro-catalyzed synthesis of 1,2,3-thiadiazoles

图式6. 电化学合成三取代的2-噁唑啉衍生物

Scheme 6. Electrosynthesis of trisubstituted 2-oxazolines

图式7. 二氧化碳、苯肼和多聚甲醛的电化学合成二唑酮类化合物

Scheme 7. Electrochemical conversion of CO2 with aryl hydrazines and paraformaldehyde into 1,3,4-oxadiazol-2(3H)-one derivatives

图式8. 多组分电化学催化合成合成1,5-二取代的三氮唑衍生物

Scheme 8. Multicomponent electro-catalyzed synthesis of 1,5- disubstituted triazoles

图式9. 碘盐为媒介电化学催化合成取代咪唑

Scheme 9. Electro-catalyzed synthesis of substituted imidazoles mediated by iodized salt

图式10. 碘盐为媒介电化学催化合成苯并噁唑的可能机理

Scheme 10. Proposed reaction mechanism for electro-catalyzed synthesis of benzoxazoles mediated by iodized salt

图式11. 电化学催化合成2-氨基苯并噁唑

Scheme 11. Electro-catalyzed synthesis of 2-aminobenzoxazoles

图式12. 碘盐媒介电化学催化N-苯基烯胺合成吲哚的可能机理

Scheme 12. Proposed reaction mechanism for electro-catalyzed synthesis of substituted indoles mediated by iodides

图式13. 电化学催化合成取代的咪唑并含氮杂环

Scheme 13. Electro-catalyzed synthesis of substituted imidazo-fused N-heterocycles

图式14. 电化学催化合成咪唑[1,2-a]并吡啶

Scheme 14. Electro-catalyzed synthesis of imidazo[1,2-a]pyri- dines

图式15. 电催化氨基取代苯乙酮合成吲哚-2,3-二酮

Scheme 15. Electrocatalytic C—H/N—H coupling of 2'-amino- acetophenones for the synthesis of isatins

图式16. 电催化邻氨基苯乙烯分子内胺氧化合成含氮杂环吲哚啉

Scheme 16. Electrochemically catalyzed amino-oxygenation of styrenes for the synthesis of indolines

图式17. 电化学催化[4+2]成环合成吡嗪衍生物

Scheme 17. Electrochemical catalysis leads to [4+2] annulation for the synthesis of pyrazines

图式18. 电化学催化合成吡啶[1,2-a]并苯并咪唑衍生物

Scheme 18. Electro-catalyzed synthesis of pyrido[1,2-a]-ben- zimidazoles

图式19. 溴盐为媒介电化学催化合成2-吲哚啉酮衍生物

Scheme 19. Electro-catalyzed synthesis of oxindoles mediated by bromides salt.

图式20. 溴盐为媒介电化学催化合成含三氟甲基官能团的2-吲哚啉酮的可能机理

Scheme 20. Proposed reaction mechanism for electro-catalyzed trifluoromethylation/cyclization of N-arylacrylamides mediated by bromides salt

图式21. 溴盐为媒介电化学催化合成吡咯烷衍生物

Scheme 21. Electro-catalyzed synthesis of pyrrolidines mediated by bromides salt.

图式22. 溴盐为媒介电化学催化合成1,2,4-三氮唑[1,5-a]吡啶的可能机理

Scheme 22. Proposed reaction mechanism for electro-catalyzed synthesis of 1,2,4-triazole[1,5-a]pyridine mediated by bromides salt

图式23. 氟盐为媒介电化学催化合成5-氟甲基-2-噁唑啉类化合物的可能机理

Scheme 23. Proposed reaction mechanism for electro-catalyzed synthesis of 5-fluoromethyl-2-azolines mediated by fluorine salt

图式24. 电化学催化炔丙基酰胺的氟环化反应

Scheme 24. Eectro-catalyzed fuorocyclization of N-popargyla- mides

参考文献 31

[1]	(a) Sabbasani, V. R.; Wang, K. P.; Streeter, M. D.; Spiegel, D. A. Angew. Chem. Int. Ed. 2019, 58, 18913. pmid: 26472902
	(b) Draghici, C.; Wang, T.; Spiegel, D. A. Science 2015, 350, 294. pmid: 26472902
	(c) Wang, S.; Huang, W.; Zhang, X.; Zhang, X.; Pan, C. Chin. J. Org. Chem. 2020, 40, 959. (in Chinese) pmid: 26472902
	(王淑琴, 黄婉云, 张小蓉, 张晓婷, 潘成学, 有机化学, 2020, 40, 959.) pmid: 26472902
	(d) Li, M.; Wang, R.; Hao, W.; Jiang, B. Chin. J. Org. Chem. 2020, 40, 1540. (in Chinese) pmid: 26472902
	(李梦帆, 王榕, 郝文娟, 姜波, 有机化学, 2020, 40, 1540.) pmid: 26472902
	(e) Zhang, F.; Peng, X.; Ma, J. Chin. J. Org. Chem. 2019, 39, 109. (in Chinese) pmid: 26472902
	(张发光, 彭星, 马军安, 有机化学, 2019, 39, 109.) pmid: 26472902
	(f) Sun, Y.; Zhou, L.; Wang, L. Chin. J. Org. Chem. 2019, 39, 3516. (in Chinese) pmid: 26472902
	(孙悦玮, 周来运, 王兰芝, 有机化学, 2019, 39, 3516.) pmid: 26472902
	(g) Meng, L.; Wang, Z.-Y. Chin. Chem. Lett. 2013, 24, 780. pmid: 26472902
[2]	(a) Ye, Z.; Zhang, F. Chin. J. Chem. 2019, 37, 513. pmid: 28451237
	(b) Liu, Z.; Zhang, Y.-S.; Wei, Y.; Shi, M. Eur. J. Org. Chem. 2020, 2020, 1093. pmid: 28451237
	(c) Sundar, S.; Rengan, R. Org. Biomol. Chem. 2019, 17, 1402. doi: 10.1039/C8OB02785D pmid: 28451237
	(d) Sridevi, B.; Kandimalla, S. R.; Reddy, B. V. S. Eur. J. Org. Chem. 2019, 2019, 6800. pmid: 28451237
	(e) Rossi, R.; Angelici, G.; Casotti, G.; Manzini, C.; Lessi, M. Adv. Synth. Catal. 2019, 361, 2737. pmid: 28451237
	(f) Roslan, I. I.; Ng, K.-H.; Jaenicke, S.; Chuah, G.-K. Catal. Sci. Technol. 2019, 9, 1528. pmid: 28451237
	(g) Parvatkar, P. T.; Manetsch, R.; Banik, B. K. Chem. Asian J. 2019, 14, 6. pmid: 28451237
	(h) Salfeena, C. T. F.; Jalaja, R.; Davis, R.; Suresh, E.; Somappa, S. B. Acs Omega 2018, 3, 8074. pmid: 28451237
	(i) Monga, A.; Bagchi, S.; Sharma, A. New J. Chem. 2018, 42, 1551. pmid: 28451237
	(j) Felipe-Blanco, D.; Gonzalez-Gomez, J. C. Adv. Synth. Catal. 2018, 360, 2773. pmid: 28451237
	(k) Donthiboina, K.; Namballa, H. K.; Shaik, S. P.; Nanubolu, J. B.; Shankaraiah, N.; Kamal, A. Org. Biomol. Chem. 2018, 16, 1720. pmid: 28451237
	(l) Chen, X.; Wang, Z.; Huang, H.; Deng, G.-J. Adv. Synth. Catal. 2018, 360, 4017. pmid: 28451237
	(m) Zhou, X.; Ma, H.; Shi, C.; Zhang, Y.; Liu, X.; Huang, G. Eur. J. Org. Chem. 2017, 2017, 237. pmid: 28451237
	(n) Tjutrins, J.; Arndtsen, B. A. Chem. Sci. 2017, 8, 1002. doi: 10.1039/c6sc04371b pmid: 28451237
	(o) Sunkari, S.; Shaik, S. P.; Krishna, N. H.; Rao, A. V. S.; Kodiripaka, B. G.; Alarifi, A.; Kamal, A. Asian J. Org. Chem. 2017, 6, 1830. pmid: 28451237
	(p) Singh, D.; Kumar, V.; Devi, N.; Malakar, C. C.; Shankar, R.; Singh, V. Adv. Synth. Catal. 2017, 359, 1213. pmid: 28451237
	(q) Saito, A. ARKIVOC 2017,84. pmid: 28451237
[3]	(a) Leech, M. C.; Lam, K. Acc. Chem. Res. 2020, 53, 121. pmid: 28991454
	(b) Jiao, K.-J.; Xing, Y.-K.; Yang, Q.-L.; Qiu, H.; Mei, T.-S. Acc. Chem. Res. 2020, 53, 300. pmid: 28991454
	(c) Yuan, Y.; Lei, A. Acc. Chem. Res. 2019, 52, 3309. pmid: 28991454
	(d) Xiong, P.; Xu, H.-C. Acc. Chem. Res. 2019, 52, 3339. pmid: 28991454
	(e) Fu, N.; Song, L.; Liu, J.; Shen, Y.; Siu, J. C.; Lin, S. J. Am. Chem. Soc. 2019, 141, 14480. pmid: 28991454
	(f) Yan, M.; Kawamata, Y.; Baran, P. S. Chem. Rev. 2017, 117, 13230. doi: 10.1021/acs.chemrev.7b00397 pmid: 28991454
[4]	(a) Xiong, P.; Xu, H.-H.; Xu, H.-C. J. Am. Chem. Soc. 2017, 139, 2956. pmid: 28199102
	(b) Yang, Y.-Z.; Wu, Y.-C.; Song, R.-J.; Li, J.-H. Chem. Commun. 2020, 56, 7585. doi: 10.1039/D0CC02580A pmid: 28199102
	(c) Luo, M.-J.; Li, Y.; Ouyang, X.-H.; Li, J.-H.; He, D.-L. Chem. Commun. 2020, 56, 2707. pmid: 28199102
	(d) Luo, M.-J.; Zhang, T.-T.; Cai, F.-J.; Li, J.-H.; He, D.-L. Chem. Commun. 2019, 55, 7251. pmid: 28199102
[5]	Tang, H.-T.; Jia, J.-S.; Pan, Y.-M. Org. Biomol. Chem. 2020, 18, 5315. pmid: 32638806
[6]	Chen, J.; Yan, W. Q.; Lam, C. M.; Zeng, C. C.; Hu, L. M.; Little, R. D. Org. Lett. 2015, 17, 986. pmid: 25654310
[7]	Wang, H.; Shi, J.; Tan, J.; Xu, W.; Zhang, S.; Xu, K. Org. Lett. 2019, 21, 9430. pmid: 31746208
[8]	Ma, H.-Y.; Zha, Z.-G.; Zhang, Z.-L.; Meng, L.; Wang, Z.-Y. Chin. Chem. Lett. 2013, 24, 780. doi: 10.1016/j.cclet.2013.05.032
[9]	Wang, Z.-Q.; Meng, X.-J.; Li, Q.-Y.; Tang, H.-T.; Wang, H.-S.; Pan, Y.-M. Adv. Synth. Catal. 2018, 360, 4043. doi: 10.1002/adsc.v360.21
[10]	Mo, S.-K.; Teng, Q.-H.; Pan, Y.-M.; Tang, H.-T. Adv. Synth. Catal. 2019, 361, 1756. doi: 10.1002/adsc.v361.8
[11]	Wang, H.; Zhang, J.; Tan, J.; Xin, L.; Li, Y.; Zhang, S.; Xu, K. Org. Lett. 2018, 20, 2505. pmid: 29664646
[12]	Yang, N.; Lai, Q.; Jiang, H.; Yuan, G. Electrochem. Commun. 2016, 72, 109. doi: 10.1016/j.elecom.2016.09.016
[13]	Yang, N.; Yuan, G. J. Org. Chem. 2018, 83, 11963. doi: 10.1021/acs.joc.8b01808 pmid: 30178990
[14]	Zeng, L.; Li, J.; Gao, J.; Huang, X.; Wang, W.; Zheng, X.; Gu, L.; Li, G.; Zhang, S.; He, Y. Green Chem. 2020, 22, 3416. doi: 10.1039/D0GC00375A
[15]	Li, W.-C.; Zeng, C.-C.; Hu, L.-M.; Tian, H.-Y.; Little, R. D. Adv. Synth. Catal. 2013, 355, 2884. 17e3498b-27fb-45af-92dd-31161d3fcee8 doi: 10.1002/adsc.201300502
[16]	Gao, W.-J.; Li, W.-C.; Zeng, C.-C.; Tian, H.-Y.; Hu, L.-M.; Little, R. D. J. Org. Chem. 2014, 79, 9613. pmid: 25255384
[17]	Tang, S.; Gao, X.; Lei, A. Chem. Commun. 2017, 53, 3354. doi: 10.1039/C7CC00410A
[18]	Qian, P.; Yan, Z.; Zhou, Z.; Hu, K.; Wang, J.; Li, Z.; Zha, Z.; Wang, Z. Org. Lett. 2018, 20, 6359. pmid: 30280901
[19]	Qian, P.; Yan, Z.; Zhou, Z.; Hu, K.; Wang, J.; Li, Z.; Zha, Z.; Wang, Z. J. Org. Chem. 2019, 84, 3148. pmid: 30648866
[20]	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
[21]	Qian, P.; Su, J. H.; Wang, Y.; Bi, M.; Zha, Z.; Wang, Z. J. Org. Chem. 2017, 82, 6434. doi: 10.1021/acs.joc.7b00635 pmid: 28535683
[22]	Liang, S.; Zeng, C.-C.; Luo, X.-G.; Ren, F.-z.; Tian, H.-Y.; Sun, B.-G.; Little, R. D. Green Chem. 2016, 18, 2222. doi: 10.1039/C5GC02626A
[23]	Liu, K.; Song, C.; Wu, J.; Deng, Y.; Tang, S.; Lei, A. Green Chem. 2019, 21, 765. doi: 10.1039/C8GC03786H
[24]	Lv, S.; Han, X.; Wang, J.-Y.; Zhou, M.; Wu, Y.; Ma, L.; Niu, L.; Gao, W.; Zhou, J.; Hu, W.; Cui, Y.; Chen, J. Angew. Chem. Int. Ed. 2020, 59, 11583. doi: 10.1002/anie.v59.28
[25]	Jiang, Y.-Y.; Liang, S.; Zeng, C.-C.; Hu, L.-M.; Sun, B.-G. Green Chem. 2016, 18, 6311. doi: 10.1039/C6GC01970F
[26]	Jiang, Y.-Y.; Dou, G.-Y.; Xu, K.; Zeng, C.-C. Org. Chem. Front. 2018, 5, 2573.
[27]	Zhang, S.; Li, L.; Xue, M.; Zhang, R.; Xu, K.; Zeng, C. Org. Lett. 2018, 20, 3443. doi: 10.1021/acs.orglett.8b00981 pmid: 29863351
[28]	Nikolaienko, P.; Jentsch, M.; Kale, A. P.; Cai, Y.; Rueping, M. Chem.-Eur. J. 2019, 25, 7177. doi: 10.1002/chem.v25.29 pmid: 30861204
[29]	Li, Y.; Ye, Z.; Chen, N.; Chen, Z.; Zhang, F. Green Chem. 2019, 21, 4035.
[30]	Haupt, J. D.; Berger, M.; Waldvogel, S. R. Org. Lett. 2019, 21, 242. pmid: 30557030
[31]	Herszman, J. D.; Berger, M.; Waldvogel, S. R. Org. Lett. 2019, 21, 7893. pmid: 31513415