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Pyrazol-3-yldiazonium Salts as Key Reagents for C–C Bond Formation and Pyrazole-Containing Heterocycle Synthesis.

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Title: Pyrazol-3-yldiazonium Salts as Key Reagents for C–C Bond Formation and Pyrazole-Containing Heterocycle Synthesis.
Authors: Barabash, Oksana V.1 (AUTHOR), Ostapiuk, Mary Y.1 (AUTHOR), Kravets, Mykola2 (AUTHOR), Obushak, Mykola D.1 (AUTHOR), Schmidt, Andreas3 (AUTHOR) schmidt@ioc.tu-clausthal.de, Ostapiuk, Yurii V.1 (AUTHOR) y.ostapiuk@gmail.com
Source: Synthesis. Aug2025, Vol. 57 Issue 15, p2351-2362. 12p.
Subjects: Pyrazolyl compounds, Heterocyclic compounds, Organic reaction mechanisms, Functional groups, Coupling reactions (Chemistry), Pyrazolates, Nucleophiles, Ring formation (Chemistry)
Abstract: A novel application of 1-methylpyrazol-3-yldiazonium salts in the Meerwein reaction was introduced. These diazonium salts reacted with α,β-unsaturated functionalized compounds under Meerwein reaction conditions to yield pyrazole-containing building blocks, which subsequently allowed cyclization reactions with bisnucleophiles for the synthesis of pyrazol-3-yl-containing heterocyclic systems. In this way, pyrazole-containing heterocyclic compounds with 2-aminothiazole, 2-aminoselenazole, thiazolidin-4-one, selenazolidin-4-one, 3-hydroxythiophene, and 3-aminothiophene rings were efficiently prepared. [ABSTRACT FROM AUTHOR]
Copyright of Synthesis is the property of Georg Thieme Verlag Stuttgart and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.)
Database: Engineering Source
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Header DbId: egs
DbLabel: Engineering Source
An: 186680723
AccessLevel: 6
PubType: Academic Journal
PubTypeId: academicJournal
PreciseRelevancyScore: 0
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  Data: Pyrazol-3-yldiazonium Salts as Key Reagents for C–C Bond Formation and Pyrazole-Containing Heterocycle Synthesis.
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  Data: <searchLink fieldCode="JN" term="%22Synthesis%22">Synthesis</searchLink>. Aug2025, Vol. 57 Issue 15, p2351-2362. 12p.
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  Data: <searchLink fieldCode="DE" term="%22Pyrazolyl+compounds%22">Pyrazolyl compounds</searchLink><br /><searchLink fieldCode="DE" term="%22Heterocyclic+compounds%22">Heterocyclic compounds</searchLink><br /><searchLink fieldCode="DE" term="%22Organic+reaction+mechanisms%22">Organic reaction mechanisms</searchLink><br /><searchLink fieldCode="DE" term="%22Functional+groups%22">Functional groups</searchLink><br /><searchLink fieldCode="DE" term="%22Coupling+reactions+%28Chemistry%29%22">Coupling reactions (Chemistry)</searchLink><br /><searchLink fieldCode="DE" term="%22Pyrazolates%22">Pyrazolates</searchLink><br /><searchLink fieldCode="DE" term="%22Nucleophiles%22">Nucleophiles</searchLink><br /><searchLink fieldCode="DE" term="%22Ring+formation+%28Chemistry%29%22">Ring formation (Chemistry)</searchLink>
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  Data: A novel application of 1-methylpyrazol-3-yldiazonium salts in the Meerwein reaction was introduced. These diazonium salts reacted with α,β-unsaturated functionalized compounds under Meerwein reaction conditions to yield pyrazole-containing building blocks, which subsequently allowed cyclization reactions with bisnucleophiles for the synthesis of pyrazol-3-yl-containing heterocyclic systems. In this way, pyrazole-containing heterocyclic compounds with 2-aminothiazole, 2-aminoselenazole, thiazolidin-4-one, selenazolidin-4-one, 3-hydroxythiophene, and 3-aminothiophene rings were efficiently prepared. [ABSTRACT FROM AUTHOR]
– Name: AbstractSuppliedCopyright
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  Data: <i>Copyright of Synthesis is the property of Georg Thieme Verlag Stuttgart and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract.</i> (Copyright applies to all Abstracts.)
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RecordInfo BibRecord:
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        Value: 10.1055/s-0043-1773546
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      – Code: eng
        Text: English
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        PageCount: 12
        StartPage: 2351
    Subjects:
      – SubjectFull: Pyrazolyl compounds
        Type: general
      – SubjectFull: Heterocyclic compounds
        Type: general
      – SubjectFull: Organic reaction mechanisms
        Type: general
      – SubjectFull: Functional groups
        Type: general
      – SubjectFull: Coupling reactions (Chemistry)
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      – SubjectFull: Pyrazolates
        Type: general
      – SubjectFull: Nucleophiles
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      – SubjectFull: Ring formation (Chemistry)
        Type: general
    Titles:
      – TitleFull: Pyrazol-3-yldiazonium Salts as Key Reagents for C–C Bond Formation and Pyrazole-Containing Heterocycle Synthesis.
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            NameFull: Barabash, Oksana V.
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            – D: 01
              M: 08
              Text: Aug2025
              Type: published
              Y: 2025
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              Value: 57
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