Synthesis of 3-Aminoquinazolinones via a SnCl 2 -Mediated ANRORC-like Reductive Rearrangement of 1,3,4-Oxadiazoles.

Herein, we developed a new SnCl 2 -mediated ANRORC (addition of nucleophile, ring-opening, and ring-closure)-like rearrangement for the synthesis of 3-amino-2-substituted-quinazolin-4(3 H )-one from 2-(2-nitrophenyl)-5-substituted-1,3,4-oxadiazole. The new method is solvent-dependent and features the use of a green solvent system (i.e., ethanol/water), high yields, and simple workup. The reduced product could be exclusively synthesized by changing the solvent to acetonitrile.