Three-component Reaction Of 4-hydroxycoumarin Research Articles

Synthesis and characterization of an Fe-MOF@Fe3O4 nanocatalyst and its application as an organic nanocatalyst for one-pot synthesis of dihydropyrano[2,3-c]chromenes.

In this study, the recyclable heterogeneous cluster bud Fe-MOF@Fe3O4 'nanoflower' composite (CB Fe-MOF@Fe3O4 NFC) was successfully synthesized using Fe(NO3)3·9H2O, 8-hydroxyquinoline sulfate monohydrate, and Fe3O4 nanoparticles by microwave irradiation. The as-prepared CB Fe-MOF@Fe3O4 NFC was characterized by X-ray diffraction (XRD), field-emission scanning electron microscopy (FE-SEM), energy-dispersive X-ray spectroscopy (EDX), vibrational sampling magnetometry (VSM), and Fourier transform infrared spectroscopy (FTIR). The CB Fe-MOF@Fe3O4 NFC samples proved to have excellent catalytic activity. The activity of the CB Fe-MOF@Fe3O4 NFC nanocatalyst was explored in the synthesis of dihydropyrano[3, 2-c]chromene derivatives via a three-component reaction of 4-hydroxycoumarin, malononitrile, and a wide range of aromatic aldehyde compounds. Optimized reaction conditions had several advantages, including the use of water as a green solvent, environmental compatibility, simple work-up, reusability of the catalyst, low catalyst loading, faster reaction time, and higher yields.

Functionalized nanoclinoptilote as a novel and green catalyst for the synthesis of Mannich bases derived from 4-hydroxy coumarin

In this research, hexamethylene tetraamine propyl silane functionalized nano clinoptilolite (NCP@SiO3PrHMTA) as a novel, green, non-toxic, low cost, heterogeneous, and reusable nanocatalyst was designed, and developed. The structure of the nanocatalyst was fully characterized using various analytical techniques, including; X-ray diffraction (XRD), Fourier transform infrared spectroscopy (FT-IR), scanning electron microscopy (SEM), transmission electron microscopy (TEM), energy-dispersive X-ray spectroscopy (EDS) and thermo gravimetric–differential thermal analysis (TG-DTA). The prepared nanocatalyst has been used as an efficient and recoverable catalyst for the synthesis of aminocoumarin Mannich bases by the three-component reaction of 4-hydroxycoumarin, aniline and aromatic aldehydes. In the presence of this novel nanocatalyst, aminocoumarin Mannich bases were obtained in excellent yields, high purity, and short reaction times under safe and clean conditions.

Sodium alginate: A biopolymeric catalyst for the synthesis of novel and known polysubstituted pyrano[3,2-c]chromenes

A library of known and new 4-aroyl-pyrano[3,2-c]chromenes have been synthesized through the one-pot, three-component reaction of 4-hydroxycoumarin, aryl glyoxals, and malononitrile or ethyl cyanoacetate in the presence of sodium alginate without any post modification, as a biopolymeric bifunctional organocatalyst, in EtOH under reflux conditions in short times. The desired products were obtained in high to excellent yields under optimized conditions. This procedure offers many advantages, such as operational simplicity, a green solvent system, short reaction times, high to excellent yields, simple work up and separation, and using a natural commercially available polysaccharide that is transition-metal-free, biodegradable and recoverable. Furthermore, sodium alginate can be recycled at least four times with negligible loss of its catalytic activity.

A new synthesis of pyrrolo[3,2-d]pyrimidine derivatives by a one-pot, three-component reaction in the presence of L-proline as an organocatalyst

Abstract A one-pot, three-component reaction of 4-hydroxycoumarin, arylglyoxals, and 6-aminouracil or 1,3-dimethyl-6-aminouracil in the presence of L-proline as an organocatalyst in acetic acid under reflux conditions provided a series of new pyrrolo[3,2-d]pyrimidine derivatives in good yields.

Solvent-free preparation of 3-aryl-2-[(aryl)(arylamino)]methyl-4H-furo[3,2-c]chromen-4-one derivatives using ZnO-ZnAl2O4 nanocomposite as a heterogeneous catalyst

Abstract The title compounds were synthesized by a three-component reaction of 4-hydroxycoumarin, aromatic amines and α,β-epoxy ketones, catalyzed by ZnO-ZnAl2O4 nanocomposite.

A highly efficient protocol for the synthesis of new 3-(α-aroylamido)-4-hydroxycoumarin derivatives using SnCl2–SiO2 nanoparticles under solvent-free conditions

An efficient and simple protocol for the synthesis of the title compounds is described via a one-pot, three-component reaction of 4-hydroxycoumarin, aryl glyoxals and amides, using SnCl2-SiO2 nanoparticles as a heterogeneous catalyst under solvent-free conditions. The advantages of this synthesis include excellent yields, mild reaction conditions, atom economy, a reusable catalyst and no need for chromatographic separations.

Green Synthesis of 4-aryl-3,4-Dihydrochromeno[3,4-e][1,3]Oxazine-2,5-Dione in Aqueous Media by Condensation of 4-Hydroxycoumarin with Aromatic Aldehydes and Methyl Carbamate

A green and efficient synthesis of the title compounds has been achieved in a one-pot, three-component reaction of 4-hydroxycoumarin and aromatic aldehydes with methyl carbamate catalysed by p-toluenesulfonic acid in aqueous media to afford 4-aryl-3,4-dihydrochromeno[3,4-e][1,3]oxazine-2,5-diones in excellent yields. The salient features of this protocol are: short reaction times, high yields and absence of any hazardous organic solvent. Consequently, this procedure could be classified as green chemistry.

Nano Clinoptilolite: Highly Efficient Catalyst for the Synthesis of Chromene Derivatives Under Solvent-Free Conditions.

An efficient and selective synthesis of substituted chromene derivatives via three-component reaction of 4-hydroxycoumarin or 1,3-dicarbonyl compounds, activated acetylenic compounds and N-nucleophiles is described. The reaction was conducted under solvent-free conditions at 70°C using potassium fluoride impregnated on natural zeolite as a cheap and available solid base. The procedure has several advantages involving selectivity, excellent yields and a convenient work-up method.

Synthesis of Functionalized Dihydrofurocoumarin Derivatives from 3-Aminoalkyl-4-hydroxycoumarin

Some dihydrofuro-fused coumarin derivatives were synthesized from 3-aminoalkyl-4-hydroxycoumarin via in situ generation of N-ylide. The 3-aminoalkylated 4-hydroxycoumarin derivatives were synthesized from one-pot, three-component reaction of 4-hydroxycoumarin, aryl aldehydes, and secondary amines in ethanol at room temperature. Again, when salicylaldehyde was employed instead of benzaldehyde, interestingly pyranocoumarins were obtained. The reaction protocol can be further explored toward the synthesis of many other heterocyclic fused dihydrofurans.

Molecular Diversity from the L-Proline-Catalyzed, Three-Component Reactions of 4-Hydroxycoumarin, Aldehyde, and 3-Aminopyrazole or 1,3-Dimethyl-6-aminouracil

The three-component reaction of 4-hydroxycoumarin, aldehyde, and aminopyrazole in the presence of a catalytic amount of L-proline in ethanol under reflux conditions provided the cyclized product (dihydrochromeno[4,3-b]pyrazolo[4,3-e]pyridine-6(7H)-one), whereas under similar reaction conditions, replacing aminopyrazole by 1,3-dimethyl-6-aminouracil provided the acyclic three-component product (6-amino-5-((4-hydroxy-2-oxo-2H-chromen-3-yl)methyl)-1,3-dimethylpyrimidine-2,4(1H,3H)-dione). This method is metal free and atom economical, and avoids column chromatographic purification as all the products can be purified by recrystallization.

One-pot, three-component synthesis of pyranocoumarins containing an aroyl group

Abstract An expeditious method to prepare pyranocoumarins containing an aroyl group by the three-component reaction of 4-hydroxycoumarin with arylglyoxals and malononitrile is described. The reaction is efficiently catalyzed by Mohr’s salt, and the products were obtained in good to excellent yields with high purity. The method is simple, inexpensive, and environmentally friendly.

Multicomponent reactions for facile access to coumarin-fused dihydroquinolines and quinolines: synthesis and photophysical studies

A three-component reaction of 4-hydroxycoumarin, aldehydes and aromatic amines in the presence of catalytic amounts of Bi(OTf)3 is reported. Photophysical studies of these molecules showed that coumarin-fused dihydroquinolines exhibit significant quantum yields.

Boric Acid–Catalyzed One-Pot Access to 7-Aryl-benzopyrano[4,3-b] benzopyran-6,8-diones Under Aqueous Micellar Conditions

A mild protocol for the synthesis of 7-arylbenzopyrano[4,3-b]benzopyran-6,8-diones by three-component reaction of 4-hydroxycoumarin, aromatic aldehyde, and 5,5-dimethylcyclohexane-1,3-dione (dimedone) with boric acid catalyst under aqueous micellar conditions is described. Good to excellent yield, high selectivity, tolerance of several common functional and protecting groups, and green features including avoidance of organic solvent in the reaction as well as isolation stage and use of nontoxic water-compatible mild Lewis acid catalyst are key attractive features of the protocol. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications® for the following free supplemental resource(s): Full experimental and spectral details.]

An efficient synthesis of novel chromeno[3′,4′:5,6]pyrano[2,3-b]indole derivatives

An efficient two-step method was described for the synthesis of chromeno[3′,4′:5,6]pyrano[2,3-b]indole derivatives. The three-component reaction of 4-hydroxycoumarin, variously substituted benzaldehydes and indolin-2-one was promoted by P2O5 in refluxing ethanol to give trimolecular adducts, which were then cyclized in 1,2-dichloroethane under reflux using POCl3.