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One-Pot Cascade Synthesis of Quinazolin-4(3H)‑ones via Nickel-Catalyzed Dehydrogenative Coupling of o‑Aminobenzamides with Alcohols

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journal contribution
posted 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 (tetramethyltetraaza[14]­annulene (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.