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Relevant academic research and scientific papers

TEMPO-mediated aerobic oxidative synthesis of 2-aryl benzoxazoles via ring-opening of benzoxazoles with benzylamines

A simple and efficient TEMPO-mediated system for aerobic oxidative synthesis of 2-aryl benzoxazoles from readily available benzoxazoles and primary benzylic and hetero benzylic amines is presented in one pot. The reaction proceeds through the ring-opening of benzoxazoles and is followed by oxidative condensation with benzylamines. These metal-free, straightforward reactions worked well with a wide range of substrates, yielding moderate to good yields under mild conditions using air as an external green oxidant.

Dowex 50W: A green mild reusable catalyst for the synthesis of 2-aryl benzoxazole derivatives in aqueous medium

In this work simple efficient, one pot and environmentally friendly method was developed for the synthesis of 2-Aryl-1H-benzoxazole derivatives at 80oC using ortho-aminophenol and various aldehydes. It has been found that Dowex 50W is an effective catalyst to prepare moderate to high yield of a variety of benzoxazole derivatives through a clean and simple process. Aqueous medium, green methodology, rapid reaction, reusability of heterogeneous catalyst are the great advantages of this protocol.

Sulfur/DABCO Promoted Reductive Coupling/Annulation Cascade Reaction between o -Hydroxy/Amino Nitrobenzenes and Benzaldehydes

Sulfur/DABCO was found to be an efficient reagent in promoting- the reductive coupling/annulation of o -nitrophenols or o -nitroanilines with benzaldehydes. This method represents a simple, straightforward, and green approach to the construction of benz-oxazoles and benzimidazoles.

Sulfur-Promoted Synthesis of Benzoxazoles from 2-Aminophenols and Aldehydes

Elemental sulfur (S8) was found to be an excellent stoichiometric oxidant to promote oxidative condensation of 2-aminophenols with a wide range of aldehydes, including aliphatic aldehyde such as cyclohexanecarboxaldehyde. The reactions were catalyzed by sodium sulfide in the presence of DMSO as an additive. The benzoxazole products were obtained in satisfactory yields. The reaction conditions could be applied to larger syntheses (10–50 mmol).

One-pot multicomponent reaction of catechols, ammonium acetate, and aldehydes for the synthesis of benzoxazole derivatives using the fe(iii)-salen complex

The Fe(III)-salen complex has been applied successfully as a catalyst for the novel, simple, efficient, and one-pot multicomponent synthesis of benzoxazole derivatives from catechols, ammonium acetate as the nitrogen source, and aldehydes (nontoxic and cheap alternatives of amines) for the first time. Using this procedure, a wide range of benzoxazoles was successfully synthesized in the presence of a catalyst in EtOH under mild conditions, and all products were obtained in excellent yields. To the best of our knowledge, this method is the first example of the multicomponent synthesis of benzoxazole derivatives using these starting materials. The notable features such as the use of air that is considered as a benign oxidant and EtOH as a green solvent, ease of product separation, readily available and inexpensive aldehydes, and mild conditions make our procedure more efficient and practical for organic synthesis. Moreover, the current protocol is successfully applied to synthesize desirable products on a large scale.

Unexpected Decarboxylation-Triggered o-Hydroxyl-Controlled Redox Condensation of Phenylglycines with 2-Nitrophenols in Aqueous Media

A decarboxylation-triggered and o-hydroxyl-controlled hydrogen-transfer strategy for the one-pot synthesis of benzoxazoles from readily available amino acids and 2-nitrophenols is reported. On the basis of this autoredox reaction, the C?N bond can be efficiently constructed to afford the desired products in moderate to good yields under transition-metal-free conditions in aqueous media. (Figure presented.).

Deep eutectic solvent-catalyzed arylation of benzoxazoles with aromatic aldehydes

A novel and efficient methodology for the arylation of benzoxazoles with aromatic aldehydes catalyzed by deep eutectic solvent has been developed. The reaction smoothly proceeded with a wide range of substrates to give the desired products in high yields within short reaction time. Deep eutectic solvents are easily recovered and reused without significant loss of catalytic activity.

Palladium(II) Immobilized Onto the Glucose Functionalized Magnetic Nanoparticle as a New and Efficient Catalyst for the One-pot Synthesis of Benzoxazoles

Palladium(II) have been immobilized into the nano magnetic Fe3O4 which was functionalized with glucose in order to achieve a one-pot synthesis of 2-substituted benzoxazole derivatives with high yields in the diverse range of organic solvents. The nano catalyst is highly dispersive in polar solvents and can be easily recovered and reused for 6 runs without significant loss of its activity. Finally, the catalyst was fully characterized by FT-IR, TGA, CHN, SEM, EDX and atomic absorption spectroscopy.

Phosphonium acidic ionic liquid: An efficient and recyclable homogeneous catalyst for the synthesis of 2-Arylbenzoxazoles, 2-Arylbenzimidazoles, and 2-Arylbenzothiazoles

A highly efficient and green strategy for the synthesis of 2-Arylbenzoxazoles, 2-Arylbenzimidazoles, and 2-Arylbenzothiazoles catalyzed by phosphonium acidic ionic liquid has been developed via the condensation of o-Aminophenol, o-phenylenediamines, and o-Aminothiophenol, respectively, with aldehydes. The reaction has a good yield, the broad substrate scope, and mild condition. Triphenyl(butyl-3-sulphonyl)phosphonium toluenesulfonate catalyst was easily obtained from cheap and available starting materials through a one-pot synthesis. Its structure was identified by 1H NMR, 13C NMR, 31P NMR, and FT-IR techniques. Other properties including thermal stability and acidity were determined by TGA and Hammett acidity function method. Interestingly, the catalyst can maintain its constantly outstanding performance till the fourth recovery.

N-Heterocyclic Carbene (NHC)-Catalyzed One-Pot Aerobic Oxidative Synthesis of 2-Substituted Benzo[ d ]oxazoles, Benzo[ d ]thiazoles and 1,2-Disubstituted Benzo[ d ]imidazoles

N-Heterocyclic carbene (NHC), generated in situ from easily available N-heterocyclic imidazolium salt with air as terminal oxidant, has successfully been utilized as a cheap and efficient catalyst for one-pot aerobic oxidative synthesis of 2-arylbenzo[ d ]oxazoles, 2-substituted benzo[ d ]thiazoles, and 1,2-disubstituted benzo[ d ]imidazoles.