Eco-friendly synthesis of diverse and valuable 2-pyridones by catalyst- and solvent-free thermal multicomponent domino reaction

Abstract

An efficient and highly eco-friendly synthesis of diverse and functionalized 2-pyridone derivatives in good yield via the thermal multicomponent reaction of 4-oxo-4H-chromene-3-carbaldehydes with 1,3-diketoesters and anilines or primary aliphatic amines under catalyst-and solvent-free conditions is described. This reaction proceeds via domino Knoevenagel condensation/Michael addition/ring opening/ring closure reactions.

Cyrene™ as a Neoteric Bio‐Based Solvent for Catalyst‐Free Microwave‐Assisted Construction of Diverse Bipyridine Analogues for Heavy‐Metal Sensing

“…We have recently explored the utility of multicomponent reactions for the facile synthesis of functionalized 2pyridones, [27] chromenopyridinone, [28] and 2-aminopyridines. [29] Moreover, the potential of the cyano group as nitrogen source for the construction of a pyridine ring system was demonstrated by a catalyst-and solvent-free thermal multicomponent cascade reaction.…”

Novel 2-Hydroselenonicotinonitriles and Selenopheno[2, 3-b]pyridines: Efficient Synthesis, Molecular Docking-DFT Modeling, and Antimicrobial Assessment

“…2-Pyridones are multifaceted compounds that are present in numerous bioactive natural products and pharmaceutical compounds (Gorobets et al, 2004 ; Mijin et al, 2014 ). Despite the availability of several conventional methods to synthesize pyridone derivatives or its use, solvent-free and environmentally safe green approaches are highly demanded as influential procedures from both the economical and synthetic point of view (Burger et al, 2002 ; Wathey et al, 2002 ; Kappe et al, 2008 ; Grundas, 2011 ; Mijin et al, 2014 ; Helmy et al, 2015 ; Poudel et al, 2015 ; Abdellattif et al, 2017 ; Hagar et al, 2020b ). Pyridone derivatives also emerged as valuable building blocks for the synthesis of bioactive natural products as well as a versatile synthon for the synthesis of diverse nitrogen-containing heterocyclic compounds like β-lactams, indolizidine alkaloid, quinolizidines, and piperidines (Burger et al, 2002 ; Potewar et al, 2008 ).…”

Ag3[PMo12O40]: An efficient and green catalyst for the synthesis of highly functionalized pyran‐annulated heterocycles via multicomponent reaction

“…[25] Regarding environmental protection from chemical industry, water and aqueous media are green solvents for use in organic transformations due to the abundance of water, as well as it being non-flammable and non-hazardous. [26] A literature survey revealed the biological significance of 2-amino-4H-chromenes having amino and nitrile moieties at the 2 and 3 positions, respectively ( Figure 1). [9,27] Because they show such a broad scope of applications, the development of an efficient, green and economically feasible method for the formation of 2-amino-3-cyano-4Hchromenes as structural motifs is still in much demand.…”

“…Nowadays, much attention has been focused on environmental control by using benign sources of energy and replacement of volatile environmentally harmful chemicals and biologically discordant common organic solvents . Regarding environmental protection from chemical industry, water and aqueous media are green solvents for use in organic transformations due to the abundance of water, as well as it being non‐flammable and non‐hazardous …”