One-pot Condensation Of 2-naphthol Research Articles

Tetramethylammonium hydroxide (TMAH) as an efficient catalyst for the one-pot synthesis of 1,2-dihydro-1-aryl- naphtho[1,2-e][1,3]oxazine-3-ones under solvent-free conditions

1,2-Dihydro-1 -arylnaphtho[1,2-e][1,3]oxazine-3-one derivatives were synthesized in high yields using an efficient and one-pot condensation of 2-naphthol, aromatic aldehydes and urea catalyzed by tetramethylammonium hydroxide (TMAH) under solvent-free conditions. KEY WORDS: TMAH, Naphthoxazine-3-one, Solvent-free reaction, 2-Naphthol, Multi-component reactions Bull. Chem. Soc. Ethiop. 2016, 30(1), 161-164.DOI: http://dx.doi.org/10.4314/bcse.v30i1.16

One-pot Synthesis of 1H-benzo[f]chromen-2-yl (phenyl)methanone Derivatives in the Presence of Copper Triflate as Catalyst Using Ultrasonic Irradiation

A rapid, efficient and environment-friendly protocol for the synthesis of naphthopyranes has been developed by one-pot condensation of 2-naphthol, various aromatic aldehydes and benzoylacetone or 1,3-diphenyl-1,3-propandione in the presence of Cu(OTf) 2 as catalyst under ultrasonic irradiation. The present approach offers the advantages of clean reaction, simple methodology, short reaction time, high yield and economic availability of the catalyst.

Efficient one-pot synthesis of 14-aryl-14H-dibenzo[a,j]xanthene derivatives promoted by niobium pentachloride

AbstractA simple and efficient procedure for the synthesis of 14-aryl-14H-dibenzo[a,j]xanthene derivatives through one-pot condensation of 2-naphthol with aryl aldehydes in the presence of niobium pentachloride is described. The reactions were carried out using 25 mole % of NbCl5, at ambient temperature, and in acceptable reaction times, affording excellent yields of the products.

Tungstophosphoric acid/zirconia composites prepared by the sol–gel method: An efficient and recyclable green catalyst for the one-pot synthesis of 14-aryl-14H-dibenzo[a,j]xanthenes

Samples of zirconia modified with different contents of tungstophosphoric acid (TPA) were synthesized from zirconium propoxide via sol–gel reactions using polyethylene glycol as template and were characterized by different physicochemical techniques (BET, XRD, FT-IR, and 31P MAS-NMR). The SBET of the solids decreases and the microporosity increases with the increase of the TPA content. According to FT-IR and 31P MAS-NMR studies, the main species present in the samples is [PW12O40]3− anion, which was partially transformed into [P2W21O71]6− and [PW11O39]7− anions during the synthesis and drying steps. The XRD patterns of the modified samples exhibit neither the characteristic peaks of TPA nor those attributed to its decomposition products.Aryl-14H-dibenzo[a,j]xanthenes have been synthesized by a one-pot condensation of 2-naphthol and aryl aldehydes, catalyzed by tungstophosphoric acid/zirconia composites in a solvent-free medium using conventional heating. The present approach offers the advantages of clean reaction, simple methodology, short reaction time, and high yield. The reaction work-up is very simple and the catalyst can be easily separated from the reaction mixture and reused several times in subsequent reactions without appreciable loss of the catalytic activity.

Green catalytic synthesis of 14-aryl-14H-dibenzo[a,j]xanthenes using recyclable mesoporous zirconia modified with tungstophosphoric acid

A simple and efficient procedure has been developed for the preparation of aryl-14H-dibenzo[a,j]xanthenes by a one-pot condensation of 2-naphthol and aryl aldehydes, in the presence of mesoporous zirconia modified with tungstophosphoric acid (ZrTPA60BT100), to be used as a heterogeneous catalyst in a solvent-free medium using conventional heating. The present approach offers the advantages of clean reaction, simple methodology, short reaction time, and high yield. The reaction work-up is very simple and the catalyst can be easily separated from the reaction mixture and reused several times in subsequent reactions without appreciable loss of the catalytic activity.

Zinc Benzenesulfonate–Promoted Eco-Friendly and Efficient Synthesis of 1-Amidoalkyl-2-naphthols

A three-component, one-pot condensation of 2-naphthol, aldehydes, and amides catalyzed by zinc benzenesulfonate gives 1-amidoalkyl-2-naphthols in good yields at 80 °C under solvent-free conditions. The catalytic activities of zinc benzenesulfoante and 12 other metal benzenesulfonates were compared. After the reaction, zinc benzenesulfoante can be recycled several times without distinct loss of catalytic activity.

An Efficient and Green One‐pot Synthesis of 12‐Aryl‐8,9,10,12‐tetrahydrobenzo[a]xanthen‐11‐one Derivatives Promoted by Sulfamic Acid in [BMIM]BF4 Ionic Liquid

AbstractAn efficient and green procedure for the synthesis of novel 12‐aryl‐8,9,10,12‐tetrahydrobenzo[a]xanthen‐11‐one derivatives has been described through one‐pot condensation of 2‐naphthol, arylaldehyde and 5,5‐dimethyl‐cyclohexane‐1,3‐dione in the presence of sulfamic acid (NH2SO3H) in ionic liquid 1‐n‐butyl‐3‐methylimidazolium tetrafluoroborate ([BMIM]BF4). These reactions proceed with good yields under short reaction time. Furthermore, the green catalytic system can be recycled specific times with no decreases in yields and reaction rates.

Ytterbium perfluorooctanoate [Yb(PFO)3]: a novel and efficient catalyst for the synthesis of tetrahydrobenzo[a]xanthene-11-ones under microwave irradiation

Ytterbium perfluorooctanoate [Yb(PFO)3] was found to be an efficient catalyst for the microwave assisted synthesis of tetrahydrobenzo[a]xanthene-11-ones by the one-pot condensation of 2-naphthol, aldehydes and 1,3-dicarbonyl compound under solvent-free conditions. The major advantages of this novel method are short reaction time, high yields, reusability of the catalyst and the absence of any volatile and hazardous organic solvents.

Poly(4-vinylpyridinium)hydrogen sulfate: A novel and efficient catalyst for the synthesis of 14-aryl-14H-dibenzo[a,j]xanthenes under conventional heating and ultrasound irradiation

A simple and convenient procedure for the synthesis of 14-aryl-14H-dibenzo[a,j]xanthenes is described through a one-pot condensation of 2-naphthol with aryl aldehydes in the presence of poly(4-vinylpyridinium)hydrogen sulfate as an efficient, cheap, readily synthesized and eco-friendly catalyst in a solvent free media using conventional heating and ultrasound irradiation.

ChemInform Abstract: Silica Supported Methanesulfonic Acid as an Efficient and Reusable Heterogeneous Catalyst for the Synthesis of Amidoalkyl Naphthols.

A green protocol for the preparation of amidoalkyl naphthols from three-component one-pot condensation of 2-naphthol, aldehydes, amides or urea in the presence of silica supported methanesulfonic acid under thermal solvent-free conditions has been described. The catalyst is stable, efficient, easily prepared, and reusable. The remarkable features of this methodology are short reaction time, excellent yields, simple experimental and work-up procedures.

ChemInform Abstract: Sodium Dodecyl Sulfate Assisted Synthesis of 1‐(Benzothiazolylamino)methyl‐2‐naphthols in Water.

An efficient synthesis of 1-(benzothiazolylamino)methyl-2-naphthols has been developed in water by one-pot condensation of 2-naphthol, aldehydes and 2-aminobenzothiazole catalyzed by sodium dodecyl sulfate. Advantages of the methodology include a very short reaction time, excellent yields and catalytic use of the sodium dodecyl sulfate.

A One-Pot synthesis of 1,2-Dihydro-1-arylnaphtho[1,2-e][1,3]oxazine-3-one Derivatives catalyzed by Perchloric Acid Supported on Silica (HClO4/SiO2) in the absence of solvent

1,2-Dihydro-1-arylnaphtho[1,2-e][1,3]oxazine-3-one derivatives were synthesized in high yields using a facile and one-pot condensation of 2-naphthol, aromatic aldehydes and urea catalyzed by perchloric acid supported on silica under thermal solvent-free conditions.

Chlorotrimethylsilane-Promoted Synthesis of 1,2-Dihydro-1-Arylnaphtho [1,2-e] [1,3]Oxazine-3-Ones

Chlorotrimethylsilane (TMSCI) is effective as a catalyst for the preparation of 1,2-dihydro-1-arylnaphtho[1,2-e] [1,3]oxazine-3- ones using a one-pot condensation of 2-naphthol, aromatic aldehydes and urea in DMF as solvent. The reaction times, temperature, and catalyst amounts were varied.

A facile approach for the synthesis of 14-aryl- or alkyl-14 H-dibenzo[ a, j]xanthenes under solvent-free condition

A facile, efficient and environment-friendly protocol for the synthesis of 14-aryl- or alkyl-14 H-dibenzo[ a, j]xanthenes has been developed by one-pot condensation of 2-naphthol with aliphatic and aromatic aldehydes in the presence of P 2O 5 or InCl 3 as catalysts under solvent-free conditions. The present approach offers the advantages of clean reaction, simple methodology, short reaction time, high yield, easy purification, and economic availability of the catalyst.

Synthesis of 14-aryl-14H-dibenzo[a,j]xanthene Derivatives Catalysed by Expanded Graphite under Solvent-Free Condition

A convenient eco-friendly procedure has been developed for the synthesis of 14-aryl-14 H-dibenzo[ a,j]xanthene derivatives by one-pot condensation of 2-naphthol and aryl aldehydes catalysed by expanded graphite under solvent-free conditions. The present methodology offers several advantages such as excellent yields, shorter reaction times, low cost and reusability of the catalyst.

One step synthesis of 14-alkyl- or aryl-14H-dibenzo[a,j]xanthenes using sodium hydrogen sulfate as catalyst

A simple and environmentally benign procedure for the synthesis of 14-alkyl- or aryl-14H-dibenzo[a,j]xanthenes is described through a one-pot condensation of 2-naphthol with aryl or alkyl aldehydes in the presence of sodium hydrogen sulfate as a catalyst under solvent-free conditions.

Ceric-sulfate-catalyzed synthesis of 14-aryl- or 14-alkyl-14H-dibenzo[aj]xanthene under conventional heating and microwave irradiation

A simple and facile procedure for the synthesis of 14-aryl- or 14-alkyl-14H-dibenzo[aj]xanthenes is described. The procedure takes place by the one-pot condensation of 2-naphthol with aldehydes in the presence of anhydrous ceric sulfate as the catalyst under solvent-free conventional heating and microwave irradiation.Key words: xanthene, one-pot condensation, aldehyde, 2-naphthol, ceric sulfate, solvent-free, microwave irradiation.