Research and Application of Pyridinium 1,4-Zwitterionic Thiolates in Organic Synthesis

doi:10.6023/cjoc202305013

Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (11): 3844-3860.DOI: 10.6023/cjoc202305013 Previous Articles Next Articles

1,4-吡啶硫内鎓盐在有机合成中的研究与应用

侯学会^a, 李议慧^b, 张庆玲^b, 刘俊桃^a, 陈亚静^b^,^*()

a 河南牧业经济学院理学部郑州 450046
b 郑州大学药学院郑州 450001

收稿日期:2023-05-12 修回日期:2023-06-14 发布日期:2023-06-26
基金资助:
国家自然科学基金(22201267); 河南省科技攻关(232102111051); 河南省科技攻关(232102110019); 河南省科技攻关(232102320289)

Research and Application of Pyridinium 1,4-Zwitterionic Thiolates in Organic Synthesis

Xuehui Hou^a, Yihui Li^b, Qingling Zhang^b, Juntao Liu^a, Yajing Chen^b()

a Faculty of Science, Henan University of Animal Husbandry and Economy, Zhengzhou 450046
b School of Pharmaceutical Sciences, Zhengzhou University, Zhengzhou 450001

Received:2023-05-12 Revised:2023-06-14 Published:2023-06-26
Contact: * E-mail: chenyj@zzu.edu.cn
Supported by:
National Natural Science Foundation of China(22201267); Key Scientific and Technological Project of Henan Province(232102111051); Key Scientific and Technological Project of Henan Province(232102110019); Key Scientific and Technological Project of Henan Province(232102320289)

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

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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.

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Fig. & Tab. 24

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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1,4-吡啶硫内鎓盐在有机合成中的研究与应用

Research and Application of Pyridinium 1,4-Zwitterionic Thiolates in Organic Synthesis

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Fig. & Tab. 24

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