Cascade SN2′–SNAr, Elimination, and 1,5-Hydride Shift Reactions by Acetylacetone/Acetoacetic Esters: Synthesis of 9,10-Dihydroacridines

Abstract

A reaction involving the use of acetylacetone/methyl acetoacetate and Morita–Baylis–Hillman acetates for the efficient, one-pot, metal-free synthesis of 9,10-dihydroacridines at room temperature was developed. The cascade of reactions involved sequential SN2′–SNAr reactions, elimination, and reduction through ketene generation and hydride transfer. Evidence for hydride shift via a ketene intermediate was also discussed. © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim