1,4-吡啶硫内鎓盐在有机合成中的研究与应用

doi:10.6023/cjoc202305013

摘要/Abstract

1,4-吡啶硫内鎓盐是一类重要的氮硫杂合成子, 其中的吡啶片段既可以作为离去基团, 也可以作为亲电反应位点参与反应, 构建多种类型的氮硫杂骨架. 因此, 近年来1,4-吡啶硫内鎓盐在含氮、含硫杂环化合物的合成应用中受到了极大的关注. 基于此, 系统综述了1,4-吡啶硫内鎓盐在两种反应模式([3+m]和[5+m]环合反应)下构建氮硫杂环的研究进展, 总结了其在环合反应及杂环化学中的应用, 并对该领域的研究前景进行了展望.

关键词: 1,4-吡啶硫内鎓盐, 环合反应, 含氮杂环, 含硫杂环

Pyridinium 1,4-zwitterionic thiolates are important sulfur- and nitrogen-containing synthons, in which the pyridine fragments can act as leaving groups, but also as electrophilic sites, constructing various types of sulfur- and nitrogen-hetero- cycles. Hence, pyridinium 1,4-zwitterionic thiolates have attracted much attention on the synthesis for N-containing and S-containing heterocyclic compounds in recent years. The progress of pyridinium 1,4-zwitterionic thiolates participated annulation via [3+m] and [5+m] modes is reviewed, their applications on constructing N- and S-heterocyclic rings are summarized, and their future prospects are discussed.

Key words: pyridinium 1,4-zwitterionic thiolates, annulation reactions, N-containing heterocycles, S-containing heterocycles

引用此文

侯学会, 李议慧, 张庆玲, 刘俊桃, 陈亚静. 1,4-吡啶硫内鎓盐在有机合成中的研究与应用[J]. 有机化学, 2023, 43(11): 3844-3860.

Xuehui Hou, Yihui Li, Qingling Zhang, Juntao Liu, Yajing Chen. Research and Application of Pyridinium 1,4-Zwitterionic Thiolates in Organic Synthesis[J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3844-3860.

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

分享此文

图/表 24

图式1. 1,4-吡啶硫内鎓盐的合成

Scheme 1. Synthesis of pyridinium 1,4-zwitterionic thiolates

图式2. 1,4-吡啶硫内鎓盐的反应模式

Scheme 2. Reaction modes of pyridinium 1,4-zwitterionic thiolates

图式3. 1,4-吡啶硫内鎓盐与二氮杂二烯的[4+3]环合反应

Scheme 3. [4+3] annulation of pyridinium 1,4-zwitterionic thiolates with diazodienes

图式4. 1,4-吡啶硫内鎓盐与活化联烯的[3+2]环合反应

Scheme 4. [3+2] annulation of pyridinium 1,4-zwitterionic thiolates with activated allenes

图式5. 1,4-吡啶硫内鎓盐与活化炔烃的[3+2]环合反应

Scheme 5. [3+2] annulation of pyridinium 1,4-zwitterionic thiolates with activated alkynes

图式6. 1,4-吡啶硫内鎓盐与单侧活化炔烃的[3+2]环合反应

Scheme 6. [3+2] annulation of pyridinium 1,4-zwitterionic thiolates with unilaterally activated alkynes

图式7. 1,4-吡啶硫内鎓盐与腙酰氯的[(3+3)-1]环合反应

Scheme 7. [(3+3)-1] annulation of pyridinium 1,4-zwitterionic thiolates with hydrazonoyl chlorides

图式8. 1,4-吡啶硫内鎓盐与氮杂邻亚甲基苯醌的[4+3]环合反应

Scheme 8. [4+3] annulation of pyridinium 1,4-zwitterionic thiolates with aza-o-quinone methides

图式9. 1,4-吡啶硫内鎓盐与1-炔基-2-萘酚或2-炔基苯酚的[4+3]环合反应

Scheme 9. [4+3] annulation of pyridinium 1,4-zwitterionic thiolates with 1-alkynylnaphthalen-2-ols or 2-alkynylphenols

图式10. 1,4-吡啶硫内鎓盐与氮杂环丙烷的[3+3]环合反应

Scheme 10. [3+3] annulation of pyridinium 1,4-zwitterionic thiolates with aziridines

图式11. 1,4-吡啶硫内鎓盐与氟代乙腈的[3+2]环合反应

Scheme 11. [3+2] annulation of pyridinium 1,4-zwitterionic thiolates with CF3CN

图式12. 1,4-吡啶硫内鎓盐与苯炔的[5+2]和[3+2]环合反应

Scheme 12. [5+2] and [3+2] annulation of pyridinium 1,4-zwitterionic thiolates with benzynes

图式13. 1,4-吡啶硫内鎓盐与α-官能团化溴代物的一锅法分步[(5+1)-1]环合反应

Scheme 13. One-pot stepwise [(5+1)-1] annulation of pyridinium 1,4-zwitterionic thiolates with α-functionalized bromoalkanes

图式14. 碱促进1,4-吡啶硫内鎓盐与丙炔酸衍生物的[(5+1)-1]环合反应

Scheme 14. Base promoted [(5+1)-1] annulation of pyridinium 1,4-zwitterionic thiolates with propiolic acid derivatives

图式15. 1,4-吡啶硫内鎓盐与联烯的[5+2]环合反应

Scheme 15. [5+2] annulation of pyridinium 1,4-zwitterionic thiolates with allenes

图式16. 1,4-喹啉硫内鎓盐与硫叶立德的串联[2+1]/[5+1]环合反应

Scheme 16. Cascade [2+1]/[5+1] annulation of quinolinium 1,4-zwitterionic thiolates with sulfur ylides

图式17. 铜催化1,4-吡啶硫内鎓盐参与的脱羧串联环化反应

Scheme 17. Cu-catalyzed pyridinium 1,4-zwitterionic thiolates participated decarboxylative cascade cyclization reactions

图式18. 可见光促进1,4-吡啶硫内鎓盐与膦酰基重氮化物的[5+1]环合反应

Scheme 18. Visible light-induced [5+1] annulation between pyridinium 1,4-zwitterionic thiolates and phosphoryl diazomethylarenes

图式19. 可见光促进1,4-吡啶硫内鎓盐与膦酰基腙的一锅法[1+5]环合反应

Scheme 19. Visible light-induced one-pot [1+5] annulation between pyridinium 1,4-zwitterionic thiolates and phosphoryl hydrazones

图式20. 1,4-吡啶硫内鎓盐与重氮化合物的[(5+1)-1]环合反应

Scheme 20. [(5+1)-1] annulation of pyridinium 1,4-thiolates and diazo compounds

图式21. 1,4-吡啶硫内鎓盐与二氟卡宾的[5+1]环合反应

Scheme 21. [5+1] annulation of pyridinium 1,4-zwitterionic thiolates with difluorocarbene

图式22. 1,4-吡啶硫内鎓盐与烷基磺酰氯的环合反应

Scheme 22. Annulation of pyridinium 1,4-zwitterionic thiolates with alkanesulfonyl chlorides

图式23. 1,4-吡啶硫内鎓盐与1-磺酰基三氮唑的环合反应

Scheme 23. Annulation of pyridinium 1,4-zwitterionic thiolates with 1-sulfonyltriazoles

图式24. 微波促进的1,4-吡啶硫内鎓盐与膦酰基重氮化合物的环合反应

Scheme 24. Microwave promoted annulation of pyridinium 1,4-zwitterionic thiolates with phosphoryl diazomethylarenes

参考文献 39

[1]	Vitaku, E.; Smith, D. T.; Njardarson, J. T. J. Med. Chem. 2014, 57, 10257. doi: 10.1021/jm501100b pmid: 25255204
[2]	Zhang, J.; Zhang, C.; Zheng, Z.; Zhou, P.; Liu, W. Chin. J. Org. Chem. 2022, 42, 2745. (in Chinese) doi: 10.6023/cjoc202204002
	(张建涛, 张聪, 郑梓栋, 周鹏, 刘卫兵, 有机化学, 2022, 42, 2745.) doi: 10.6023/cjoc202204002
[3]	Bhorali, P.; Sultana, S.; Gogoi, S. Asian J. Org. Chem. 2022, 11, e202100754. doi: 10.1002/ajoc.v11.4
[4]	Sundaravelu, N.; Sangeetha, S.; Sekar, G. Org. Biomol. Chem. 2021, 19, 1459. doi: 10.1039/d0ob02320e pmid: 33528480
[5]	Xiao, L.; Liu, G.; Ren, P.; Wu, T.; Lu, Y.; Kong, J. Chin. J. Org. Chem. 2022, 42, 1002. (in Chinese) doi: 10.6023/cjoc202109038
	(肖立伟, 刘光灿, 任萍, 吴彤桐, 卢玉伟, 孔洁, 有机化学, 2022, 42, 1002.) doi: 10.6023/cjoc202109038
[6]	Moafi, L.; Ahadi, S.; Khavasi, H. R.; Bazgir, A. Synthesis 2011, 1399.
[7]	Cheng, B.; Wang, T. In Encyclopedia of Reagents for Organic Synthesis, Wiley-Interscience, Hoboken, 2021, pp. 1-4.
[8]	Wang, Z.-H.; You, Y.; Zhao, J.-Q.; Zhang, Y.-P.; Yin, J.-Q.; Yuan, W.-C. Molecules 2023, 28, 3059. doi: 10.3390/molecules28073059
[9]	Huang, J.; Zhang, L.; Meng, X. Org. Chem. Front. 2023, 10, 2813. doi: 10.1039/D3QO00228D
[10]	Cheng, B.; Li, Y.; Wang, T.; Zhang, X.; Li, H.; Li, Y.; Zhai, H. Chem. Commun. 2019, 55, 14606. doi: 10.1039/C9CC08326J
[11]	Zhai, S.; Zhang, X.; Cheng, B.; Li, H.; Li, Y.; He, Y.; Wang, T.; Zhai, H. Chem. Commun. 2020, 56, 3085. doi: 10.1039/D0CC00262C
[12]	Cheng, B.; Duan, X.; Li, Y.; Zhang, X.; Li, H.; Wu, F.; Li, Y.; Wang, T.; Zhai, H. Eur. J. Org. Chem. 2020, 1896.
[13]	Wang, T.; Zhu, X.; Tao, Q.; Xu, W.; Sun, H.; Wu, P.; Cheng, B.; Zhai, H. Chin. Chem. Lett. 2021, 32, 3972. doi: 10.1016/j.cclet.2021.04.021
[14]	Cheng, B.; Bao, B.; Xu, W.; Li, Y.; Li, H.; Zhang, X.; Li, Y.; Wang, T.; Zhai, H. Org. Biomol. Chem. 2020, 18, 2949. doi: 10.1039/d0ob00224k pmid: 32242607
[15]	Yang, B.; Gao, S. Chem. Soc. Rev. 2018, 47, 7926. doi: 10.1039/C8CS00274F
[16]	Liao, H.-H.; Minoza, S.; Lee, S.-C.; Rueping, M. Chem.-Eur. J. 2022, 28, e202201112. doi: 10.1002/chem.v28.46
[17]	Happy, S.; Junaid, M.; Yadagiri, D. Chem. Commun. 2023, 59, 29. doi: 10.1039/D2CC05623B
[18]	Wang, C.-C.; Liu, X.-H.; Wang, X.-L.; Cui, H.-P.; Ma, Z.-W.; Ding, D.; Liu, J.-T.; Meng, L. Chen, Y.-J. Adv. Synth. Catal. 2022, 364, 296. doi: 10.1002/adsc.v364.2
[19]	Zhang, L.; Fang, L.; Huang, H.; Wang, C.; Gao, F.; Wang, Z. J. Org. Chem. 2021, 86, 18156. doi: 10.1021/acs.joc.1c02433
[20]	He, Y.; Wu, P.; Zhang, X.; Wang, T.; Tao, Q.; Tao, Q.; Zhou, K.; Ouyang, Z.; Zhai, H.; Cheng, D.-J.; Cheng, B. Org. Chem. Front. 2022, 9, 4612. doi: 10.1039/D2QO00735E
[21]	Wang, C.-C.; Yang, Y.-T.; Wang, Q.-L.; Liu, X.-H.; Chen, Y.-J. Org. Chem. Front. 2022, 9, 4271. doi: 10.1039/D2QO00612J
[22]	Yao, Y.; Lin, B.; Wu, M.; Zhang, Y.; Huang, Y.; Han, X.; Han, X.; Weng, Z. Org. Biomol. Chem. 2022, 20, 8761. doi: 10.1039/D2OB01749K
[23]	Cheng, B.; Li, Y.; Wang, T.; Zhang, X.; Li, H.; He, Y.; Li, Y.; Zhai, H. J. Org. Chem. 2020, 85, 6794. doi: 10.1021/acs.joc.0c00374 pmid: 32329339
[24]	Cheng, B.; Zhang, X.; Li, Y.; Li, H.; He, Y.; Li, Y.; Wang, T.; Zhai, H. Chem. Commun. 2020, 56, 8396. doi: 10.1039/D0CC03446K
[25]	Singh, G. S.; Mmatli, E. E. Eur. J. Med. Chem. 2011, 46, 5237. doi: 10.1016/j.ejmech.2011.08.042
[26]	Sharma, V.; Kumar, V. Med. Chem. Res. 2014, 23, 3593. doi: 10.1007/s00044-014-0940-1
[27]	Kim, E.; Lee, Y.; Lee, S.; Park, S. B. Acc. Chem. Res. 2015, 48, 538. doi: 10.1021/ar500370v
[28]	Cheng, B.; Li, H.; Duan, S.; Zhang, X.; He, Y.; Li, Y.; Wang, T.; Zhai, H. Org. Biomol. Chem. 2020, 18, 6253. doi: 10.1039/d0ob01398f pmid: 32756728
[29]	Cheng, B.; Zhang, X.; Li, H.; He, Y.; Li, Y.; Sun, H.; Wang, T.; Zhai, H. Adv. Synth. Catal. 2020, 362, 4668. doi: 10.1002/adsc.v362.21
[30]	Jin, Q.; Jiang, C.; Gao, M.; Zhang, D.; Hu, S.; Zhang, J. J. Org. Chem. 2021, 86, 15640. doi: 10.1021/acs.joc.1c02175
[31]	Li, T.-T.; You, Y.; Sun, T.-J.; Zhang, Y.-P.; Zhao, J.-Q.; Wang, Z.-H.; Yuan, W.-C. Org. Lett. 2022, 24, 5120. doi: 10.1021/acs.orglett.2c01959
[32]	Sun, S.; Wei, Y.; Xu, J. Org. Lett. 2022, 24, 6024. doi: 10.1021/acs.orglett.2c02321
[33]	Wei, Y.; Sun, S.; Xu, J. Tetrahedron Lett. 2023, 120, 154444. doi: 10.1016/j.tetlet.2023.154444
[34]	Monreal-Corona, R.; Díaz-Jiménez, À; Roglans, A.; Poster, A.; Pla-Quintana, A. Adv. Synth. Catal. 2023, 365, 760. doi: 10.1002/adsc.v365.5
[35]	Li, W.; Wang, H.; Zhang, Y.; Zhao, L.; Guo, P.; Cao, H.; Liu, X. J. Org. Chem. 2023, 88, 7199. doi: 10.1021/acs.joc.3c00447
[36]	Sun, S.; Wei, Y.; Xu, J. Org. Lett. 2023, 25, 2868. doi: 10.1021/acs.orglett.3c00842
[37]	Cheng, B.; Li, Y.; Zhang, X.; Duan, S.; Li, H.; He, Y.; Li, Y.; Wang, T.; Zhai, H. Org. Lett. 2020, 22, 5817. doi: 10.1021/acs.orglett.0c01888 pmid: 32648762
[38]	Duan, S.; Chen, C.; Chen, Y.; Jie, Y.; Luo, H.; Xu, Z.-F.; Cheng, B.; Li, C.-Y. Org. Chem. Front. 2021, 8, 6962. doi: 10.1039/D1QO01237A
[39]	Sun, S.; Wei, Y.; Xu, J. Chem. Commun. 2023, 59, 239. doi: 10.1039/D2CC05483C