An efficient Pd(ii)-catalyzed direct O-alkenylation of 2-arylquinazolinones with simple ketone-derived N-tosylhydrazones is reported. In this reaction, O-alkenylquinazolines were obtained in good yields, with excellent functional group tolerance. Pd-carbene migratory insertion is proposed as the key step in the reaction mechanism.
on the occasiono fh is 75 th birthday.Abstract: One single catalyst, [RuCl 2 (p-cymene)] 2 ,w as used for oxidative dehydrogenation followed by cross-coupling/ annulation reactions to access diversely decorated N-fused polycyclic heteroarenes from dihydroquinazolinones and al-kynes. This one-pot method does not requirep urification of intermediates or addition of coppers alts. The synergistic use of molecular oxygen as the oxidant highlights the sustainable aspectoft his method.Scheme1.Ru II -catalyzed, amide-directedcross-coupling/annulation and our work.[a] R.
Dirhodium(II) acetate‐catalyzed reactions of N‐tosylhydrazones with dihydroquinazolinones bearing different types of NH bonds that give N3‐benzyl/alkyl‐2‐arylquinazolin‐4(3H)‐ones through Csp3N bond formation by oxidative dehydrogenation and insertion of rhodium‐carbenoid into amide NH bond are reported for the first time. This method features good to excellent yields, good functional group tolerance, high regioselectivity and readily available starting materials.magnified image
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