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Base-Promoted [4 + 2] Annulation Reaction of In Situ-Generated Azadienes from N-Propargylamines with Active Methylene Compounds: Access to Highly Functionalized 2-Pyridones

Bipin Kumar Behera, Pallav Jyoti Arandhara, Bikoshita Porashar, Surjya Kumar Bora, Anil K. Saikia*

*Department of Chemistry, Indian Institute of Technology Guwahati, Guwahati 781039, India, Email: asaikiaiitg.ac.in

B. K. Behera, P. J. Arandhara, B. Porashar, S. K. Bora, A. K. Saikia, J. Org. Chem., 2023, 88, 15041-15059.

DOI: 10.1021/acs.joc.3c01478



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Abstract

A facile and efficient [4 + 2] annulation of in situ generated azadienes from N-propargylamines and active methylene compounds provides structurally diversified 2-pyridones in good yields. The developed methodology is applicable for the direct and formal synthesis of various bioactive molecules.

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proposed mechanism


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Key Words

2-pyridones


ID: J42-Y2023