An Efficient, Convenient, and Solvent-Free Synthesis of 2,3-Dihydroquinazolin-4(<i>1 H</i>)-ones Using Montmorillonite-KSF Clay as a Heterogeneous Catalyst

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.

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An Efficient, Convenient, and Solvent-Free Synthesis of 2,3-Dihydroquinazolin-4(1 H)-ones Using Montmorillonite-KSF Clay as a Heterogeneous Catalyst

Cited by 10 publications

References 14 publications

Mesoporous SBA-15@n-Pr-THAM-ZrO organic–inorganic hybrid: as a highly efficient reusable nanocatalyst for the synthesis of polyhydroquinolines and 2,3-dihydroquinazolin-4 (1h)-ones

Mesoporous SBA-15@n-Pr-THAM-ZrO organic–inorganic hybrid: as a highly efficient reusable nanocatalyst for the synthesis of polyhydroquinolines and 2,3-dihydroquinazolin-4 (1h)-ones

Pyromellitic acid grafted to cross-linked LDH by dendritic units: An efficient and recyclable heterogeneous catalyst for green synthesis of 2,3-dihydro quinazoline and dihydropyrimidinones derivatives

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

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