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Tandem Transformation of Indazolones to Quinazolinones through Pd-Catalyzed Carbene Insertion into an N-N Bond

Chikkagundagal K. Mahesha, Somnath Arjun Borade, Disha Tank, Kiran Bajaj, Himanshi Bhambri, Sanjay K. Mandal and Rajeev Sakhuja*

*Department of Chemistry, Birla Institute of Technology and Science, Pilani, Pilani 333031, Rajasthan, India, Email:

C. K. Mahesha, S. A. Borade, D. Tank, K. Bajaj, H. Bhambri, S. K. Mandal, R. Sakhuja, J. Org. Chem., 2023, 88, 1457-1468.

DOI: 10.1021/acs.joc.2c02437

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The reaction of aldehydic N-tosylhydrazones with 1-aryl- and 2-aryl-1,2-dihydro-3H-indazol-3-ones provides 1,2-di(hetero)aryl- and 2,3-di(hetero)aryl-2,3-dihydroquinazolin-4(1H)-ones, respectively through a cascade process involving base-mediated Pd-carbenoid generation nucleophilic attack of indazolone on the Pd-carbenoid complex, and intramolecular ring expansion via N-N bond cleavage.

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proposed mechanisms

Key Words

Indazolones, 2,3-Dihydroquinazolinones

ID: J42-Y2023