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]
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Database: Engineering Source
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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]
ISSN:00397881
DOI:10.1055/s-0043-1773546