One-Pot Synthesis of Pyrrolo[1,2-a]quinolin-1-ones by the Cyclocondensation of 5-Hydroxy-1-arylpyrrolidin-2-ones with Dicarbonyls

Abstract

A one-pot synthesis of pyrrolo[1,2-a]quinolin-1-ones has been developed from the reactions of 5-hydroxy-1-arylpyrrolidin-2-ones with 1,3-dicarbonyl compounds under the promotion of H3PO4/P2O5 or HOAc/H2SO4. The pyrrolo[1,2-a]quinolin-1-ones are formed by two-step reactions, that is, the coupling of N-acyliminium ion intermediates produced from 5-hydroxy-1-arylpyrrolidin-2-ones with 1,3-dicarbonyls and subsequent Friedel–Crafts reactions of the resulting ketone with the aryl ring.