InCl3-catalyzed three-component reaction: a novel synthesis of dihydropyrano[3,2-b]chromenediones under solvent-free conditions

Reddy, B. V. Subba; Reddy, M. Ramana; Narasimhulu, G.; Yadav, J. S.

doi:10.1016/j.tetlet.2010.08.044

Cited by 56 publications

(20 citation statements)

References 16 publications

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“…For further optimization of reaction conditions, we tested acetonitrile, water and ethanol/water mixtures as solvents ( Table 1, entries [14][15][16][17], and found that the desired product was obtained at a higher yield in C 2 H 5 OH 95 % ( Table 1, entry 17). In addition, in view of the benefits of solvent-free conditions, we attempted to perform the model reaction under these conditions, but found that the reaction mixture was solidified, and the results showed that the reaction under these conditions was not efficient (Table 1, entries 18).…”

Section: Resultsmentioning

confidence: 99%

“…Because of the phenol-like properties of kojic acid, most of its MCRs involve the enolic moiety of this compound [16]. Threecomponent reaction of kojic acid, aldehyde and 1,3-dione has been achieved to afford dihydropyrano [3,2-b]chromenedione derivatives [17]. A series of novel pyrano- [3, 2-b]pyrazolo [4,3-e]pyridin-8(1H)-ones were synthesized via three-component condensation of kojic acid, 1-H-pyrazol-5-amines and aldehydes [18].…”

Section: Introductionmentioning

confidence: 99%

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Eco-friendly one-pot, three-component synthesis of novel derivatives of kojic acid by the Mannich-type reaction under solvent-free ball-milling conditions

Teimuri‐Mofrad

Shahrisa

Gholamhosseini-Nazari

et al. 2015

Res Chem Intermed

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A novel series of aminokojic acid derivatives were efficiently synthesized by one-pot condensation of kojic acid, aromatic aldehydes and heteroaromatic amines in the presence of cerium(III) sulphate as an efficient and recyclable catalyst in ball-milling under solvent-free conditions at room temperature. This synthesis method offers several advantages, including a green and eco-friendly protocol, operational simplicity, mild reaction conditions, short reaction time, higher yields and easy workup procedures. The workup of these very clean reactions involves only a simple washing with acetone/cold water. The catalytic system can be reused several times with no loss of activity. Graphical Abstract O HO

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Eco-friendly one-pot, three-component synthesis of novel derivatives of kojic acid by the Mannich-type reaction under solvent-free ball-milling conditions

Teimuri‐Mofrad

Shahrisa

Gholamhosseini-Nazari

et al. 2015

Res Chem Intermed

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“…In 2010, a novel type of InCl 3 ‐catalyzed three‐component reaction was developed by Reddy and colleagues . This MCR consumes kojic acid, an aldehyde, and a 1,3‐dione to effectively produce the corresponding dihydropyrano[3,2‐ b ]chromenediones under solvent‐free conditions for 70–95 min in excellent yields.…”

Section: Mcrs Of Curcuminmentioning

confidence: 99%

Curcuminoids in Multi‐Component Synthesis

Ajavakom

Yutthaseri

Chantanatrakul

et al. 2017

Journal of Heterocyclic Chem

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The introduction of a 1,3‐dicarbonyl unit in curcuminoid derivatives for multi‐component reactions (MCRs) to furnish six‐membered heterocyclic compounds has been reviewed. Attention has focused on the assembly of the three‐component Biginelli reactions relating to curcumin or tetrahydrocurcumin (THC), aromatic aldehydes and urea as substrates. The hybrid molecules of two bioactive agents were designed and synthesized by using these MCRs concepts. The four‐component modified Hantzsch condensation was the latest development of this synthetic route. The possible mechanism of the MCRs of both curcumin and THC were also summarized.

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“…Dihydropyrano[3,2‐ b ]chromenediones (DHPCs), which are considered 4H‐chromenes, are an important class of fused oxygenated heterocycles that are synthesized via a one‐pot three‐component reaction of kojic acid, an aldehyde and a 1,3‐dione (Figure ). These heterocyclic compounds display considerable structural diversity, including a strategic alcoholic hydroxyl functional group (–CH 2 OH), which in turn can be modified by attaching biological functional groups to develop more potent drug molecules.…”

Section: Introductionmentioning

confidence: 99%

Inhibition of tyrosinase by 4H‐chromene analogs: Synthesis, kinetic studies, and computational analysis

et al. 2017

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Inhibition of mushroom tyrosinase was observed with synthetic dihydropyrano[3,2-b]chromenediones. Among them, DHPC04 displayed the most potent tyrosinase inhibitory activity with a K value of 4 μm, comparable to the reference standard inhibitor kojic acid. A kinetic study suggested that these synthetic heterocyclic compounds behave as competitive inhibitors for the L-DOPA binding site of the enzyme. Furthermore, molecular modeling provided important insight into the mechanism of binding interactions with the tyrosinase copper active site.

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InCl3-catalyzed three-component reaction: a novel synthesis of dihydropyrano[3,2-b]chromenediones under solvent-free conditions

Cited by 56 publications

References 16 publications

Eco-friendly one-pot, three-component synthesis of novel derivatives of kojic acid by the Mannich-type reaction under solvent-free ball-milling conditions

Eco-friendly one-pot, three-component synthesis of novel derivatives of kojic acid by the Mannich-type reaction under solvent-free ball-milling conditions

Curcuminoids in Multi‐Component Synthesis

Inhibition of tyrosinase by 4H‐chromene analogs: Synthesis, kinetic studies, and computational analysis

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