Cerium(III)-Catalyzed Facile Synthesis of Dihydrobenzofuran-Tethered Pyridines and Dihydroquinolin-5(6H)-ones from β-Enaminones

Abstract

A series of novel dihydrobenzofuran-tethered pyridines, dihydroquinolin-5(6H)-ones, and indeno[1,2-b]pyridin-5-ones were synthesized in very good yields by CeCl₃˙7H₂O-NaI catalyzed one-pot condensation of variants of the Bohlmann-Rahtz reaction, viz. β-enaminones derived from 7-acetyldihydrobenzofurans, acyclic and cyclic 1,3-dicarbonyls, and ammonium acetate. The protocol offers the advantages of easily accessible substrates, shorter reaction times, and easy work-up with a readily available catalyst. Further more, dihydrobenzofuran-substituted 2-(chloromethyl)pyridine was derivatized to its synthetic hybrid by reacting with piperazine.

Bohlmann-Rahtz reaction - dihydrobenzofuran - CeCl₃˙7H₂O-NaI - one-pot condensation - β-enaminone - hetero­cycles - pyridines - quinolinones

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CCDC-771475 (3aa) and CCDC-771476 (3ae) contain the crystallographic data and can be obtained free of charge from the Cambridge Crystallographic Data centre via www.ccdc.cam.ac.uk/data_request/cif.