One-Pot Cascade Synthesis of Quinazolin-4(3H)‑ones via Nickel-Catalyzed Dehydrogenative Coupling of o‑Aminobenzamides with Alcohols
journal contributionposted on 27.06.2017, 00:00 by Seuli Parua, Siuli Das, Rina Sikari, Suman Sinha, Nanda D. Paul
In this paper, we report a general, efficient, and environmentally benign method for the one-pot cascade synthesis of quinazolin-4(3H)-ones via acceptorless dehydrogenative coupling of o-aminobenzamide with alcohols catalyzed by a simple Ni(II) catalyst, [Ni(MeTAA)], featuring a tetraaza macrocyclic ligand (tetramethyltetraazaannulene (MeTAA)). A wide variety of substituted quinazolin-4(3H)-ones were synthesized in high yields starting from readily available benzyl alcohols and o-aminobenzamides. Several controlled reactions along with deuterium labeling studies were carried out to establish the acceptorless dehydrogenative nature of the reactions.