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Synthesis
DOI: 10.1055/a-2726-4076
Paper

Iron Promoted Ring Opening and Ring Closing Cascade (ROCC) Reaction of C3-(2-(phenylethynyl)phenyl)isoxazoles Leading to 3-Imino-1,3-diphenylpropenols and Isoindolin-1-ylidene Derivatives

Autoren

  • Manoranjan Behera 

    1   Chemistry Services, Aragen Life Sciences Private Limited, Hyderabad, India (Ringgold ID: RIN28557)

  • Ramakrishna Gudipati

    1   Chemistry Services, Aragen Life Sciences Private Limited, Hyderabad, India (Ringgold ID: RIN28557)

  • Raghavulu Karri

    2   Chemistry, GVK Bio, Hyderabad, India (Ringgold ID: RIN28557)

  • Jayaram Vankudoth

    3   Biochemistry, Albert Einstein College of Medicine, New York, United States (Ringgold ID: RIN2006)

  • Mallesham Poosa

    4   Chemistry, GVK Biosciences Pvt Ltd, Hyderabad, India (Ringgold ID: RIN28557)

  • Keloth Basu

    5   Department of Inorganic and Analytcial Chemistry, Andhra University, Visakhapatnam, India (Ringgold ID: RIN28548)

  • Krishna S Ethiraj

    1   Chemistry Services, Aragen Life Sciences Private Limited, Hyderabad, India (Ringgold ID: RIN28557)
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The study reports the efficient synthesis of different functionalized isoindolin-1-ylidene derivatives through FeCl3/Li2CO3 mediated cleavage of isoxazole. The highlight of the work is the sequential reductive ring-opening of C3-(2-(phenylethynyl)phenyl)ortho-alkynyl-isoxazole and intramolecular 5-exo-dig cyclization of ortho-alkynyl-isoxazole. Additionally, we reported that Fe/NH4Cl could be used to generate 3-imino-1,3-dipheylpropenols from isooxazole. Using this protocol, densely substituted N-heterocyclic compounds can be assembled in simple and efficiently. This is the first report for the synthesis of isoindolin-1-ylidene derivatives using FeCl3/Li2CO3 using isoxazole as starting material



Publikationsverlauf

Eingereicht: 04. September 2025

Angenommen nach Revision: 17. Oktober 2025

Accepted Manuscript online:
17. Oktober 2025

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