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

Hou, Xuehui; Li, Yihui; Zhang, Qingling; Liu, Juntao; Chen, Yajing

doi:10.6023/cjoc202305013

Chinese Journal of Organic Chemistry

2023

DOI: 10.6023/cjoc202305013

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

Xuehui Hou,

Yihui Li,

Qingling Zhang

et al.

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2024

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Cited by 3 publications

References 34 publications

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Assembly of Thiazino[3,4‐a]Isoquinoline and Thiazepino[5,4‐a]Isoquinoline Frameworks from Isoquinolinium 1,4‐Zwitterionic Thiolates Through [5+1] and [5+2] Cycloaddition Reactions

Wang,

Zou

et al. 2024

Eur J Org Chem

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Two cycloaddition modes of isoquinolinium 1,4‐zwitterionic thiolates have been established. Upon choosing α‐bromo ketones as the counterpart, a range of isoquinoline‐fused thiazines can be attained with yields ranging from moderate to excellent through a formal [5 + 1] reaction pathway, exhibiting remarkable substrate adaptability and resilience to diverse functional groups. Additionally, a library of unprecedented thiazepino[5,4‐a]isoquinolines, a novel category of seven‐membered heterocycles, has been synthesized via a [5 + 2] pathway utilizing acetylenedicarboxylate as the reactive component. Notably, this reaction process stands out for its exceptional 100% atomic utilization efficiency.

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Assembly of Thiazino[3,4‐a]Isoquinoline and Thiazepino[5,4‐a]Isoquinoline Frameworks from Isoquinolinium 1,4‐Zwitterionic Thiolates Through [5+1] and [5+2] Cycloaddition Reactions

Wang,

Zou

et al. 2024

Eur J Org Chem

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Synthesis of 1,4-oxathiins via [3+3] annulation of pyridinium 1,4-zwitterionic thiolates with iodonium ylides

Niu,

Pi,

et al. 2024

Green Synthesis and Catalysis

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Sc(OTf)3-catalyzed alkyne-carbonyl metathesis-initiated cyclization for accessing naphtho[2,1-b]furan-1-ones under microwave heating

Li,

Liu,

et al. 2024

Tetrahedron Letters

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

Cited by 3 publications

References 34 publications

Assembly of Thiazino[3,4‐a]Isoquinoline and Thiazepino[5,4‐a]Isoquinoline Frameworks from Isoquinolinium 1,4‐Zwitterionic Thiolates Through [5+1] and [5+2] Cycloaddition Reactions

Assembly of Thiazino[3,4‐a]Isoquinoline and Thiazepino[5,4‐a]Isoquinoline Frameworks from Isoquinolinium 1,4‐Zwitterionic Thiolates Through [5+1] and [5+2] Cycloaddition Reactions

Synthesis of 1,4-oxathiins via [3+3] annulation of pyridinium 1,4-zwitterionic thiolates with iodonium ylides

Sc(OTf)3-catalyzed alkyne-carbonyl metathesis-initiated cyclization for accessing naphtho[2,1-b]furan-1-ones under microwave heating

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