Moisture compatible and recyclable indium (III) chloride catalyzed and microwave assisted efficient route to substituted 1H-quinolin-2-ones

Abstract

An efficient three component synthesis of highly functionalized 4-methyl-1H-quinolin-2-ones in one-pot from readily available coumarin, hydrazine and isatin catalyzed by a recyclable and moisture compatible InCl 3 under microwave irradiation has been developed. The synthesis involves a InCl 3 catalyzed dehydrative nucleophilic substitution on the lactone moiety of coumarin by the isatin hydrazone resulting in the formation of N-substituted lactams, 6-substituted-4-methyl-1-(2-oxo-1,2-dihydroindol-3-ylidenamino)-1H-quinolin-2-ones.The coumarin based transformation into substituted 1H-quinolin-2-ones proceeded smoothly with quantitative yields at ambient temperature.

A Decade of Indium‐Catalyzed Multicomponent Reactions (MCRs)

“…The indium(III) chloride catalyzed three‐component reaction between 4‐methylcoumarins, isatins, and hydrazine under microwave irradiation was explored by Siddiqui et al .. These synthetic processes, undertaken in short reaction times, allow the preparation of oxindole‐4‐methyl‐1 H ‐quinolin‐2‐one derivatives (12 examples) in excellent yields, via a dehydrative nucleophilic substitution on the coumarin heterocycle by the in situ formed isatin hydrazone (Scheme ) …”

Synthesis and structural features of indium(iii) furan-2-thiocarboxylates showing efficient catalytic activity toward multicomponent reactions via Knoevenagel condensation

“…Indium (III) based catalysts have been explored on several multicomponent reactions such as classical Ugi reaction, 15,16 epoxide-based Passerini reaction, 17 multiple isocyanide insertion reactions, 18 A 3 -coupling reaction, 19 Knoevenagel-initiated MCR, [20][21][22][23][24][25][26] and Hantzsch-type dihydropyridine and pyrrole synthesis, 27 and multi-catalytic systems and nanocatalysts for the synthesis of poly-substituted heterocycles, 28,29 quinoline derivatives and amino carbazole derivatives. [30][31][32][33][34][35][36][37] However, the In(III) complexes with S/O donor ligandcatalyzed MCRs are scanty. Therefore, in the present manuscript, we report the Knoevenagel and Knoevenagel-initiated multicomponent coupling reactions.…”

Recent Advances of Indium(III) Chloride Catalyzed Reactions in Organic Synthesis

“…Multicomponent one‐pot synthesis like α‐amino phosphonates, [7] α‐amino nitriles, [8] α‐amino‐γ‐lactones [9] has been observed employing catalytic amount of InCl 3 . Moreover, InCl 3 mediated construction of sugar fused N ‐aryltetrahydropyridine, [10] antibacterial and antifungal agent 2‐substituted aryl(indolyl)kojic acid derivatives, [11] tetrahydropyridines, [12] amidoalkyl naththols, [13] chremenone‐ and quinoline‐ annulated imidazole derivatives [14] and quinolines [15] using microwave has been accomplished by the multicomponent reaction (MCR) strategy. InCl 3 supported on silica gel has been used for electrophilic amination of arenes with diethyl azodicarboxylate [16] .…”