Diacetoxyiodobenzene-mediated oxidative addition of 1,3-dicarbonyl compounds to olefins: an efficient one-pot synthesis of 2,3-dihydrofuran derivatives
A library of dihydropyrimidinones was synthesized via a “one-pot” three component Biginelli reaction using different aldehydes in combination with β-dicarbonyl compounds and urea. Selected 2-thiooxo and 2-imino analogs were also obtained with the Biginelli reaction from thiourea and guanidine hydrochloride, respectively. The products were screened in vitro for their β-secretase inhibitory activity. The majority of the compounds resulted to be active, with IC50 in the range 100 nM–50 μM.
A practical one-pot synthesis of tetrahydroquinoxalines from readily available 2-amino(nitro)anilines and 1,2-dicarbonyl compounds mediated by diboronic acid with water as both a solvent and a hydrogen donor under metal-free conditions has been discovered.
One Pot Synthesis of Micromolar BACE-1 Inhibitors Based on the Dihydropyrimidinone Scaffold and Their Thia and Imino Analogues