Cs <sub>2</sub> CO <sub>3</sub> ‐Promoted aza‐Michael Addition of ( <i>E</i> )‐ <i>β</i> ‐Iodovinyl Sulfones with 5‐Amino‐1 <i>H</i> ‐pyrazole‐4‐carbaldehydes and Anthranilic Acids/Amides: Synthesis of 5‐Sulfonylpyrazolo[3,4‐ <i>b</i> ]pyridines and

Abstract Metal‐free tandem synthesis of 5‐sulfonyl‐pyrazolo[3,4‐ b ]pyridines and 3‐sulfonyl‐4‐quinolones is accomplished by reacting 5‐amino‐1 H ‐pyrazole‐4‐carbaldehydes/carboxylic acids and anthranilic acids/amides independently with ( E )‐ β ‐iodovinyl sulfones in presence of Cs 2 CO 3 involving [4+2] cycloaddition. The reaction proceeds via an aza‐Michael addition followed by intramolecular cyclization forming a new C─N and C─C bonds. This is the first protocol to synthesize title products using ( E )‐ β ‐iodovinyl sulfones as a key synthon.

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Publication Details

Journal
Asian Journal of Organic Chemistry
Published
2025-04-07
DOI
https://doi.org/10.1002/ajoc.202400778
Citations
3
Primary Topic
Organic and Inorganic Chemical Reactions
Type
article
Field-Weighted Citation Impact
2.27
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article

Cs 2 CO 3 ‐Promoted aza‐Michael Addition of ( E )‐ β ‐Iodovinyl Sulfones with 5‐Amino‐1 H ‐pyrazole‐4‐carbaldehydes and Anthranilic Acids/Amides: Synthesis of 5‐Sulfonylpyrazolo[3,4‐ b ]pyridines and

A. Krishnaiah, Jagadeesh Babu Nanubolu, Nagaraju Medishetti, Bhanu Prasad Banda
3 citations
Asian Journal of Organic Chemistry
Organic and Inorganic Chemical Reactions
2.27
article

Cs 2 CO 3 ‐Promoted aza‐Michael Addition of ( E )‐ β ‐Iodovinyl Sulfones with 5‐Amino‐1 H ‐pyrazole‐4‐carbaldehydes and Anthranilic Acids/Amides: Synthesis of 5‐Sulfonylpyrazolo[3,4‐ b ]pyridines and

A. Krishnaiah, Jagadeesh Babu Nanubolu, Nagaraju Medishetti, Bhanu Prasad Banda
article en
3 citations

Abstract

Abstract Metal‐free tandem synthesis of 5‐sulfonyl‐pyrazolo[3,4‐ b ]pyridines and 3‐sulfonyl‐4‐quinolones is accomplished by reacting 5‐amino‐1 H ‐pyrazole‐4‐carbaldehydes/carboxylic acids and anthranilic acids/amides independently with ( E )‐ β ‐iodovinyl sulfones in presence of Cs 2 CO 3 involving [4+2] cycloaddition. The reaction proceeds via an aza‐Michael addition followed by intramolecular cyclization forming a new C─N and C─C bonds. This is the first protocol to synthesize title products using ( E )‐ β ‐iodovinyl sulfones as a key synthon.

Asian Journal of Organic ChemistryVol. 14(6)
Indian Institute of Chemical Technology (IN), Academy of Scientific and Innovative Research (IN)
Openalex Percentile: Top 13%
Organic and Inorganic Chemical Reactions
2.27
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