Indanedione structural motifs are widely distributed in natural products, pharmaceuticals and functional materials. In particular, 1,3-indanedione has attracted considerable attention due to easy ...availability and versatile reactivity for various organic transformations. In fact, recent years have witnessed a number of novel strategies for the construction of diverse annulated systems involving 1,3-indanediones. The present review emphasizes recent (2015–2021) applications of 1,3-indanedione in organic transformations to build fused- and spiro scaffolds. In this regard, synthesis of a variety of nitrogen- and oxygen containing fused heterocyclic systems are illustrated. Formation of several complex spiro-heterocycles/carbocycles has also been highlighted. In most cases, reaction mechanisms are highlighted for better understanding of reaction pathway. Significantly, the reactions described in this review involve readily available starting materials, cheap catalysts, one-pot under mild conditions and environmentally benign. Some of the reactions have been effective for the synthesis of biologically active heterocycles.
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•This review emphasizes recent applications of 1,3-indanedione to build fused- and spiro scaffolds.•Facile synthesis of nitrogen- and oxygen containing fused heterocyclic systems are highlighted.•Formation of complex spiro-heterocycles/carbocycles has also been described.•Some of the reactions are useful for the synthesis of biologically active heterocycles.
•Metal free.•Visible light initiated.•Room temperature.•Oxidative coupling.•Multicomponent synthesis.
In the most recent research, a straightforward, effective, and environmentally friendly method ...for producing spiroindoline-3,4′-quinoline was developed in ethanol using a photocatalyst eosin y and a 22 W LED lamp. This method involves the oxidative coupling of indole with enaminone and malononitrile. This method's key features include the absence of metals, low cost, environmental friendliness, greenness, non-toxicity, ease of handling, and use of renewable energy like visible light. This method exhibits a wide substrate scope for indole and active methylene compounds, including different enaminones. For the first time, spiro compounds were produced using visible light-mediated metal-free multicomponent synthesis under benign reaction conditions.
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•One-pot synthesis of 3-styryl-1H-quinoxalin-2-ones in an aqueous medium is described.•Reaction medium consists in o-phenylenediamine, sodium pyruvate and aldehydes.•Procedure is ...easily performed and applied to an interesting scope with good yields.•A mechanistic proposal involved sequential condensation reactions is presented.
A multicomponent synthesis of substituted 3-styryl-1H-quinoxalin-2-ones is described. Sequential reactions of o-phenylenediamine with sodium pyruvate and aldehydes in 20% aqueous acetic acid containing sodium acetate provided the target products in good to high yields. The reaction is proposed to proceed via initial condensation of the diamine and pyruvate partners followed by an aldol condensation-type mechanism.
An efficient method for the synthesis of densely substituted 2-oxo dihydropyrroles has been demonstrated by clean, reusable, and heterogeneous catalyst titanium dioxide (TiO2) nanopowder by the four ...component coupling reaction of dialkyl but-2-ynedioate, two different amines, and an aldehyde. The reaction is site-selective with respect to aromatic and aliphatic amines. Environmentally benign reaction procedure, excellent yields, tolerance of varieties of functionalities in the reactants, a wide variety of products and reusability of the catalyst make the methodology highly beneficial for the synthesis of polyfunctional dihydropyrroles.
Glycine is a commercially available, mild, less toxic, zwitterionic amino acid. The present review summarizes all the reported protocols related to the one-pot multicomponent synthesis of ...structurally diverse biologically promising heterocyclic scaffolds using a catalytic amount of glycine or its complexes as catalyst under various reaction conditions.
A three-component reaction for the synthesis of novel 3-heteroaryl-coumarin utilizing acetylcoumarin synthon under ultrasonic irradiation was developed using chitosan-grafted poly(vinylpyridine) as ...an eco-friendly catalyst. The process is a simple, facile, efficient procedure for the preparation of compounds displaying a thiazole ring linked to coumarin moiety. Moreover, all the products were evaluated for their anticancer activities against HEPG2-1. The results revealed that three new compounds showed promising anticancer activities.
We report efficient synthetic methodologies for the preparation of 3-amino and 3-hydroxy 3-pyrrolin-2-ones (unsaturated γ-lactams) through a multicomponent reaction of amines, aldehydes and acetylene ...or pyruvate derivatives. The densely substituted γ-lactam substrates show in vitro cytotoxicity, inhibiting the growth of the carcinoma human tumor cell lines RKO (human colon epithelial carcinoma), SKOV3 (human ovarian carcinoma) and A549 (carcinomic human alveolar basal epithelial cell). In view of the possibilities for the diversity of the substituents that offer a multicomponent, synthetic methodology, an extensive structure-activity profile is presented. In addition, the bioisosteric replacement of the flat ester group by a tetrahedral phosphonate or phosphine oxide moiety in γ-lactam substrates leads to increased growth inhibition activity. Cell morphology analysis and flow cytometry assays indicate that the main pathway by which our compounds induce cytotoxicity is based on the activation of the intracellular apoptotic mechanism.
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•Multicomponent synthesis of 1,2,3 triazoles from aromatic aldehydes, sodium azide and nitromethane.•Reusable catalytic heterogeneous system.•Microwave assisted synthesis.
The acid ...properties of Al-MCM-41 and sulfated zirconia were used to develop a strategy for the synthesis of 4-aryl-NH-1,2,3-triazoles via a multicomponent reaction involving various benzaldehydes, sodium azide and nitromethane. The efficiency of the process is analysed from the perspective of the difference in acids among the catalysts used.
The semiconducting properties and applications of three dimensional (3D) covalent organic frameworks (COFs) are greatly hampered because of their long‐ranged non‐conjugated skeletons and relatively ...unstable linkages. Here, a robust imidazole‐linked fully conjugated 3D covalent organic framework (BUCT‐COF‐7) is synthesized through the one‐pot multicomponent Debus‐Radziszewski reaction of the saddle‐shaped aldehyde‐substituted cyclooctatetrathiophene, pyrene‐4,5,9,10‐tetraone, and ammonium acetate. The semiconducting BUCT‐COF‐7, as a metal‐free catalyst, shows excellent two electron oxygen reduction reaction (ORR) activity in alkaline medium with high hydrogen peroxide (H2O2) selectivity of 83.4 %. When the BUCT‐COF‐7 as cathode catalyst is assembled into the electrolyzer, the devices showed high electrochemical production rate of H2O2 up to 326.9 mmol g−1 h−1. The accumulative amount of H2O2 could totally degrade the dye methylene blue via Fenton reaction for wastewater treatment. This is the first report about intrinsic 3D COFs for efficient electrochemical synthesis of H2O2, revealing the promising applications of fully conjugated 3D COFs in the environment‐related field.
A robust imidazole‐linked fully conjugated 3D covalent organic framework was synthesized via the one‐pot Debus‐Radziszewski multicomponent reaction. The material showed excellent two electron oxygen‐reduction activity and when it was used as cathode catalyst and assembled into the electrolyzer, the devices showed high electrochemical production rate of H2O2 up to 326.9 mmol g−1 h−1.
•The multicomponent synthesis of a hexahydroquinoline compound was performed.•β-cyclodextrin inclusion complexes were prepared to increase aqueous solubility.•Complexes demonstrated to have a slower ...release improving its biological properties.
Multicomponent synthesis are convergent reactions in which three or more starting materials react in a single step to form the product. In the discovery and development of new drugs, multicomponent reactions offer several advantages over traditional synthesis: shorter experiment time, less need for laboratory techniques and scalability. Thus, the objective of this work was to perform the multicomponent synthesis of a hexahydroquinoline compound whose pharmacological activity has been described previously. The synthesis product was characterized by spectroscopic techniques such as Fourier transform infrared spectrometry and 1H, 13C and HMQC nuclear magnetic resonance (NMR). The mechanism of the reaction was proposed to include a conjugated Michael addition. Subsequently, inclusion complexes (ICs) at 1:1 and 1:2 stoichiometries were prepared with the appropriate cyclodextrin to increase the aqueous solubility and bioavailability of this molecule. Kneading and lyophilization (LYO) methods were used to prepare the inclusion complexes, which were evaluated by phase solubility and 1H NMR spectroscopy, with LYO at a 1:2 stoichiometry having the best results. The ICs were then characterized by differential scanning calorimetry, near-infrared spectroscopy and in vitro dissolution tests, which verified a slower release of the compound with the potential to improve its biological properties.
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