Development of a Water-Mediated and Catalyst-Free Green Protocol for Easy Access to a Huge Array of Diverse and Densely Functionalized Pyrido[2,3-d:6,5-d′]dipyrimidines via One-Pot Multicomponent Reaction under Ambient Conditions

Abstract

A water-mediated and catalyst-free simple protocol for easily accessing a huge array of pharmaceutically interesting and diversely functionalized 5-alkyl/aryl/heteroaryl-10-alkyl/aryl-2,8-dioxo/dithioxo-9,10-dihydropyrido[2,3d:6,5-d′]dipyrimidine-4,6(1H,3H,5H,7H)-dione derivatives 4 (4-1−4-42) and 5,5′-(1,4-phenylene)bis(10-alkyl/aryl-2,8dioxo/dithioxo-9,10-dihydropyrido[2,3-d:6,5-d′]dipyrimidine-4,6(1H,3H,5H,7H)-dione) 4′ (4′-1−4′-8) has been developed based on a one-pot multicomponent reaction between barbituric/N,N-dimethylbarbituric/2-thiobarbituric acids (1), substituted amines (2), and aldehydes (3) under ambient conditions. The salient features of this protocol are the clean reaction profile, use of no added catalyst, water as reaction media, mild reaction conditions at room temperature, energyefficiency, easy isolation of products, no need of column chromatographic purification, high atom-economy and low E-factor, good to excellent yields, and reusability of reaction media.

A Green Method Synthesis and Antimicrobial Activity of 2-Amino-4H-Chromene Derivatives

“…Surprisingly, our local variety WEB solution application explored in the cyclocondensation of three component reaction for chromene synthesis. The authors also developed and employed other greener reagents derived from agro-waste ash for the synthesis of chromene as well as other bioactive molecule synthesis [5,51]. Firstly, we started with the optimization of green catalyst for the model reaction compound 3a, initial with zero to the 5 mL with interval of 1 mL and found the minimum amount required 3 mL of WEB solution, gave best yield even after increase the volume.…”

Ecofriendly and Facile One‐Pot Multicomponent Synthesis of 5‐Phenyl‐5,10‐dihydropyrido[2,3‐d : 6,5‐d′]dipyrimidine‐2,4,6,8(1H,3H,7H,9H)‐tetraone Derivatives Catalyzed by CuII Immobilized on Functionalized Magnetic Mesoporous MCM‐41 (Fe3O4@MCM‐41‐GPTMS‐Gu‐CuII)

“…,7H,9H)-tetraone derivatives which have attracted considerable attention due to their broad spectrum of promising biological activities and medicinal applications. [25] Numerous reports represent anticorrosive, [26] antimicrobial, [27] antitubercular, [28] antiviral, and cytotoxic activities [29] of these compounds (Scheme 1). Moreover, a few numbers of such derivatives have significant α-glucosidase and α-amylase inhibitory activity.…”

A Facile Synthetic Route to Biologically Relevant Substituted 1,4‐Naphthoquinonyl‐2‐oxoindolinylpyrimidines Under Metal‐Free Organocatalytic Conditions

“…Combinations of barbituric/thiobarbituric acid moiety with either istains, or lawsone were previously reported to generate diverse kinds of new series of molecular hybrids under varying reaction conditions involving the use of catalysts and additives, organic solvents, heating/refluxing, microwaves, electrolysis, etc . Very recently, our group also demonstrated a couple of room temperature‐based catalyst‐free synthetic routes, to novel series of N ‐ and O ‐heterocyclic molecular hybrids employing barbituric/thiobarbituric acid and lawsone as reactants among others. In continuation of our synthetic endeavors for promising molecular hybrids under green chemistry approach, we herein wish to report a convenient, clean, facile practical method for the synthesis of a series of substituted 5‐(3‐(3‐hydroxy‐1,4‐naphthoquinon‐2‐yl)‐2‐oxoindolin‐3‐yl)pyrimidine‐2,4,6(1 H ,3 H ,5 H )‐triones derivatives ( 4 ) from the one‐pot multi‐component reaction between isatins ( 1 ), 2‐hydroxy‐1,4‐naphthoquinone ( 2 ), and barbituric acid ( 3 ) using sulfamic acid as an eco‐friendly organocatalyst in aqueous ethanol under reflux.…”