A novel multi-component approach to the synthesis of pyrrolo[2,1-a]isoquinoline derivatives

Abstract

A route towards pyrrolo[2,1-a]isoquinolines through a 3CR of 1-aroyl dihydroisoquinolines, activated alkynes and alcohols has been developed.

A Three‐Component Synthesis of 3‐Functionally Substituted 5,6‐Dihydropyrrolo[2,1‐a]isoquinolines

“…Thus, 3-alkoxy-5,6-dihydroisoquinolines having an ester and acetyl group at position 2 were obtained. [24] Later, two-component transformations of 1-aroyl-3,4-dihydroisoquinolines with symmetric alkynes in aprotic solvents were described, leading to the formation of rearrangement products and transfer of the aryl group -1-oxopyrrolo[2,1-a]isoquinolines. Therefore, continuing our study on the domino reactions of 1-aroyl-3,4-dihydroisoquinolines with the participation of electron-deficient alkynes, we assumed that the anionic center of the zwitterion, which was formed at the first stage of such transformations, can react with CH-acids of various nature.…”

In Situ Generation of Quinolinium Ylides from Diazo Compounds: Copper-Catalyzed Synthesis of Indolizine

“…As well as pyrrolo­[1,2- a ]­quinoline, pyrrolo­[2,1- a ]­isoquinoline derivatives are also the focus of this research. With the optimized reaction conditions established (see Table S1), we investigated the generality and limitations of representative substrates containing synthetically useful functional groups.…”

Recent progress in the synthesis of pyrrolo[2,1-a]isoquinolines

“…35 Voskressensky and coworkers have achieved a novel threecomponent protocol with unsubstituted isoquinolines, activated alkynes and alcohols for the preparation of pyrroloisoquinolines (Scheme 23). 36 Aroyl-3,4-dihydroisoquinoline was proposed to react with methylpropionate or acetylacetylene to give a tricyclic intermediate through the Michael/intramolecular aldol cascade. A final substitution with alcohol provided the desired products (12 examples, 25-82% yields).…”