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

Serendipitous and expedite transformation of 1-aryl- and 2-aryl-1,2-dihydro-3H-indazol-3-ones to 1,2-di­(hetero)­aryl- and 2,3-di­(hetero)­aryl-2,3-dihydroquinazolin-4­(1H)-ones, respectively, was achieved in high efficiency by reacting them with aldehydic N-tosylhydrazones. The protocol proceeded t...

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Bibliographic Details
Published in:Journal of organic chemistry 2023-02, Vol.88 (3), p.1457-1468
Main Authors: Mahesha, Chikkagundagal K., Borade, Somnath Arjun, Tank, Disha, Bajaj, Kiran, Bhambri, Himanshi, Mandal, Sanjay K., Sakhuja, Rajeev
Format: Article
Language:English
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Summary:Serendipitous and expedite transformation of 1-aryl- and 2-aryl-1,2-dihydro-3H-indazol-3-ones to 1,2-di­(hetero)­aryl- and 2,3-di­(hetero)­aryl-2,3-dihydroquinazolin-4­(1H)-ones, respectively, was achieved in high efficiency by reacting them with aldehydic N-tosylhydrazones. The protocol proceeded through a cascade process involving base-mediated Pd-carbenoid generation by the decomposition of N-tosylhydrazones, nucleophilic attack of indazolone on the Pd-carbenoid complex, and intramolecular ring expansion via N–N bond cleavage. The utility of the strategy is demonstrated toward the synthesis of bioactive NPS 53574, a calcium receptor antagonist.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.2c02437