An Amino Sugar Promoted Green Protocol: A One‐Pot, Meglumine‐Catalyzed, Multicomponent Strategy for Synthesis of Multifaceted Pyrroloacridin‐1(2H)‐one Derivatives

Abstract

A concise and convenient meglumine catalysed, multicomponent, one pot synthetic pathway for pyrroloacridine via 1,3 diketones, aniline and isatin in ethanol:water mixed solvent system has been proposed. Use of an enviromentally benign catalyst, meglumine, an amino sugar was preferred due to remarkable properties such as being inexpensive, recyclable, physiologically inactive and biodegradable. Green reaction condition, broad substrate scope, operational simplicity, incorporation of an eco‐efficient catalyst, formation of C−N bond and high yields of product are some important hallmarks of the proposed strategy.

Sodium gluconate: An efficient organocatalyst for the synthesis of dihydropyrano[2,3-c] pyrazole derivatives

“…The use of n-hexane and toluene, gave poor yield ( Table 1, entries, 16,17). Polar protic solvents like ethanol, methanol gave a moderate yield as compare to polar aprotic solvents (DMF, acetonitrile) ( Table 1, entries, [12][13][14][15]. It may possible that the slight solubility of sodium gluconate in ethanol and methanol affects the catalytic activity and polar protic solvents favour the formation of Knovenagel condensation and cyclization type of reactions.…”

“…The direct use of commercially available biomolecules as a catalyst makes the processes simple and efficient and gains the significance over the conventional catalytic system, since their biocompatibility and known inclusive data about non-toxic nature allow them to enter into the category of catalyst and accepted as an environmentally suitable methodology. In this regard, great efforts have been performed to use different biomolecules like chitosan [10], β-cyclodextrinmonosulphonic acid [11], meglumine [12], starch [13], cellulose [14], and sodium alginates [15] as catalytic systems.…”

Engaging Isatins in Multicomponent Reactions (MCRs) – Easy Access to Structural Diversity

“…Meglumine is an amino sugar obtained from sorbitol, a biomass‐derived sugar alcohol, [264] and was applied as organocatalyst to synthesize the same type of pyrroloacridin‐1‐(2 H )‐one derivatives (11 examples) in yields similar to the other methodologies (Scheme 131D). Despite the higher catalyst load, meglumine required longer reaction times, when compared to the other two catalytic systems reported, but proved to be efficient in a similar reaction, in which dimedone was replaced by cyclohexane‐1,3‐dione (Scheme 131E), affording tricyclic aromatic derivatives (2 examples), under the same eco‐friendly conditions [265] …”

Advances in Heterogeneously Catalytic Degradation of Biomass Saccharides with Ordered-Nanoporous Materials

“…As a renewable carbon-based source, biomass derivatives (e.g., biodiesel, − 2,5-furan dicarboxylic acid, , and aspirin) can substitute for most fossil fuel-derived products such as polymer materials, fuels, and pharmaceutics. − In addition, various biomass carbohydrates are largely applied as additives in the food industry . Especially, saccharides used as platform intermediates make the conversion routes of lignocellulosic biomass more manifold. − …”