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February 2, 20260 citationsOpen Access

Coupling Reactions of Aryldiazonium Salt. Part-Xiii: Cinnaoline Precursors Using Chemoselective Condensation of Substituted Diazonium Salt With Acetylacetone

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CSC. J. Patil1*, A. N. Dhake1, Anil H. Shinde2, Chunilal Pawara3, Balsing B. Valvi1, Lalsing R. Vasave1, Nandu R. Vasave1, Kalpesh S. Salve1

Key Points

  • This research aims to synthesize cinnoline precursors using aryldiazonium salts and evaluate their antibacterial properties.
  • Synthesized aryldiazonium salts and coupled them with acetylacetone.
  • Characterized the compounds using TLC, UV-Vis, FTIR, and 1H NMR techniques.
  • Evaluated the antibacterial activity of the final products against ciprofloxacin.
  • Synthesized compounds C-1 to C-6 as potential cinnoline precursors.
  • Measured antibacterial activity showed moderate efficacy compared to ciprofloxacin.

Abstract

The aryldiazonium salt, Ar-N2⊕ClΘ are highly reactive compounds. It was used as intermediate in different reactions. In this work we have synthesized the varied aryldiazonium salt and coupled with an Active Methylene Group (AMG) containing compound viz. Pentane-2,4-dione or Acetyl acetone(AA). The synthesized compounds were characterized using TLC, UV-Vis, FTIR and 1H NMR techniques to arrive at the designated structures of the products formed. The final products formed, C-1 to C-6, were potentially used as precursors for synthesis of cinnoline or derivatives thereof. These compounds were tested for the antibacterial activity showed moderate activity than ciprofloxacin.

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Cite This Study

C. J. Patil1*, A. N. Dhake1, Anil H. Shinde2, Chunilal Pawara3, Balsing B. Valvi1, Lalsing R. Vasave1, Nandu R. Vasave1, Kalpesh S. Salve1 (2026) studied this question.

synapsesocial.com/papers/6980feb9c1c9540dea8110cdhttps://doi.org/10.5281/zenodo.18426944
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Also Consider

Synapse has enriched 5 closely related papers on similar clinical questions. Consider them for comparative context:

  1. 1C–H/N–H Annulation of <i>N</i> -Aryl Triazolinediones with Diazo Compounds: A Route to Cinnoline Analogues2025
  2. 2Azo-Povarov Cycloaddition of <i>N</i>-Carbonyl Aryldiazenes with <i>cis</i>,<i>trans</i>-Cycloocta-1,5-diene as a Fluorogenic Click Reaction for the Synthesis of Cinnoline Derivatives.2026
  3. 3Annulation of α-Diazo Sulfonium Salts with α-Vinylanilines via a Dicationic Intermediate toward Quinolines.2025
  4. 4Electrochemical Oxidative N–N Coupling to Construct Benzo[ <i>c</i> ]cinnolines and Azoarenes2025
  5. 5Metal-free Microwave-Assisted Azo-Povarov Reaction of N-Carbony Aryldiazenes with trans-Cyclooctene to access Ring-fused Cinnolines2024 · 1 citations