Combinatorial Synthesis of Pyrrolo[3,2-f]quinoline and Pyrrolo[3,2-a]acridine Derivatives via a Three-Component Reaction under Catalyst-Free Conditions

Abstract

A combinatorial synthesis of pyrrolo[3,2-f]quinoline and pyrrolo[3,2-a]acridine derivatives is described as a three-component reaction of aromatic aldehyde, 1H-indol-5-amine, and 1,3-dicarbonyl compounds under catalyst-free conditions. The 1,3-dicarbonyl compounds include 5,5-dimethylcyclohexane-1,3-dione, cyclopentane-1,3-dione, and 2H-indene-1,3-dione. It is interesting that the designed reactions gave aromatized or unaromatized products, which depend on the reaction temperature and reactants of 1,3-dicarbonyl compounds.

Three‐component one‐pot synthesis of pyrazino[2,3‐a]acridine derivatives under catalyst‐free conditions

“…Based on our previous research experience, [ 28,29 ] quinoxalin‐6‐amine ( 1, 1.0 mmol), 4‐chlorobenzaldehyde ( 2a, 1.0 mmol), and 5,5‐dimethylcyclohexane‐1,3‐dione ( 3a, 1.0 mmol) were treated in refluxing EtOH under catalyst‐free conditions firstly, this one‐pot three‐component reaction gave the expected 12‐(4‐chlorophenyl)‐9,9‐dimethyl‐8,9,10,12‐tetrahydropyrazino[2,3‐ a ]acridin‐11(7 H )‐one ( 4a ) in 92% yield (Scheme 1).…”

Palladium-Catalyzed Regioselective Alkoxylation via C-H Bond Activation in the Dihydrobenzo[c]acridine Series

“…Acridines and related derivatives represent an important class of aza-polycyclic compounds that have attracted considerable interest in the last century because of their broad range of properties and applications. For example, acridines are well-known as antibacterial, antimalarial, and anticancer agents [1][2][3], and have also been used in pigments, dyes, and sensor devices for decades [4]. More recently, acridine motifs have found additional applications such as cell imaging probes [5], catalysis [6], Organic Light-Emitting Diodes (OLEDs) [7] and organic semiconductors [8].…”

Facile one‐pot synthesis of a series of 7‐aryl‐8H‐benzo[h]indeno[1,2‐b]quinoline‐8‐one derivatives catalyzed by cellulose‐based magnetic nanocomposite

“…Indenoquinolines are one of the most important groups of quinoline derivatives that have a wide range of medicinal activities such as anticancer, anti ‐ inflammatory, anti ‐ tumour and inhibitor of steroid reductase, etc. Therefore, much effort have been focused on the synthesis of indenoquinoline skeletons from new, simple and direct methods . Most of the literature reports require refluxing systems, organic solvents, expensive catalysts, multiple steps and tedious work ‐ up procedures .…”