Convenient access to 5-arylisoindolo[2,1- $${\varvec{a}}$$ a ]quinolin-11(6a $${\varvec{H}}$$ H

Abstract

Substituted isoindoloquinolinones were obtained from N-aryl-3-hydroxyisoindolinones and aryl alkynes under Lewis acid-catalyzed conditions in 30-99% yields.

Diastereoselective multicomponent synthesis of dihydroisoindolo[2,1-a]quinolin-11-ones mediated by eutectic solvents

“…The easy isolation of the crude product, the recyclability and reusability of the DES together with the scalability of this methodology for the preparation of the target compound are key factors that highlight the benets of this synthetic procedure over other reported methodologies. [49][50][51][52][53]…”

“…47 Furthermore, the in situ formation of a dienophile by a one-pot gold-catalysed hydroalkoxylation of alkynols and subsequent Povarov reaction with N -aryl imines or in situ generated iminium has been developed for the obtention of [3,2- c ]quinoline derivatives. 48 Finally, the synthesis of isoindolo[2,1- a ]quinolin-11-ones have been achieved by cyclization from N -aryl-3-hydroxyisoindolinones and N -vinyl lactams or aryl alkynes under BF 3 ·Et 2 O catalysed reaction, 49–51 and by the reaction between anilines, dienophiles and 2-formylbenzoic acid (Scheme 1). 52,53…”

“…Furthermore, the in situ formation of a dienophile by a one-pot gold-catalysed hydroalkoxylation of alkynols and subsequent Povarov reaction with N-aryl imines or in situ generated iminium has been developed for the obtention of [3,2-c]quinoline derivatives. 48 Finally, the synthesis of isoindolo[2,1-a]quinolin-11-ones have been achieved by cyclization from N-aryl-3hydroxyisoindolinones and N-vinyl lactams or aryl alkynes under BF 3 $Et 2 O catalysed reaction, [49][50][51] and by the reaction between anilines, dienophiles and 2-formylbenzoic acid (Scheme 1). 52,53 All these synthetic efforts demonstrate the utility of the imino-Diels-Alder reaction in the obtention of ring-fused tetrahydroquinoline derivatives, however, environmental concerns regarding the impact of solvents and catalysts employed in this reaction demand the development of new methodologies.…”