Fast Synthesis of Substituted N‐Phenylanthranilic Acids Using Ullmann Condensation Under Microwave Irradiation in Dry Media

Martín, Ana; Mesa, Miriam; Docampo, Maite L.; Gómez, Victoria; Pellón, Raiza Texidor

doi:10.1080/00397910500374955

Cited by 15 publications

(4 citation statements)

References 3 publications

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“…The Ullmann-type condensation reaction between orthochlorobenzoic acid and aniline to form N-phenylanthranilic acid is well-known, and over the years several modifications have been made in order to provide milder, faster and more environment friendly reaction conditions with improved yields (Pellón et al 1993;Docampo Palacios and Pellón Comdom 2003;Martín et al 2006). The most recently described method uses solvent-free conditions with microwave irradiation (Martín et al 2006).…”

Section: Resultsmentioning

confidence: 98%

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Synthesis of substituted diphenylamines and carbazoles: phototransformation products of diclofenac

Svanfelt

Krönberg

2009

Environ Chem Lett

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The formation of stable and potentially hazardous compounds as a result of photochemical transformation of pharmaceutical substances in the aquatic environment implies a demand for standard compounds within environmental analysis. The major phototransformation products of diclofenac are comprised of substituted diphenylamines and carbazoles. Substituted diphenylamines were synthesized by Ullmann condensation reactions between anilines and halobenzenes. Monochlorocarbazoles were obtained from palladium-catalyzed intramolecular coupling reactions of monochlorinated diphenylamines, photocyclization of dichlorinated diphenylamines or by direct chlorination of carbazole. The availability of synthetic photoproducts of diclofenac is of critical importance for further studies on the environmental fate as well as the ecotoxicological effects of the drug in the environment.

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Section: Resultsmentioning

confidence: 98%

“…The most recently described method uses solvent-free conditions with microwave irradiation (Martín et al 2006). Synthesis of D-7 and D-3 was achieved in a microwave oven operating at 300 W (Fig.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of substituted diphenylamines and carbazoles: phototransformation products of diclofenac

Svanfelt

Krönberg

2009

Environ Chem Lett

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“…N -Phenylanthranilic acid ( 12 ) and its derivatives have been evaluated as anti-inflammatory agents. They also serve as key intermediates for acridones and acridines that possess bioactive properties such as anti-HIV, antibacterial, and antifungal activities . The original protocol reported by Ullmann involved rather harsh conditions of heating a mixture of 10 and 11 in the presence of a stoichiometric amount of Cu at 210 °C .…”

Section: Applications In Route Design Process Development and Scale-u...mentioning

confidence: 99%

Cu-Mediated Ullmann-Type Cross-Coupling and Industrial Applications in Route Design, Process Development, and Scale-up of Pharmaceutical and Agrochemical Processes

Yang

Zhao

2022

Org. Process Res. Dev.

128

116

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Cu-mediated Ullmann-type cross-coupling has experienced significant advances over the last century since the seminal publication by Ullmann in 1901. These advances have significantly expanded the scope of the original classical Ullmann coupling of aryl halides for formation of diaryl compounds to include the formation of carbon−heteroatom and other carbon− carbon bonds. The introduction of bidentate ligands drastically improved the performance of this class of transformations to enable milder reaction conditions that can tolerate a wide range of sensitive functional groups. Recent development of more powerful second-generation bidentate ligands has further allowed the coupling of less reactive aryl chlorides to proceed smoothly and realized low catalyst and ligand loadings for a broad scope of Ullmann-type cross-coupling reactions. As a result of these breakthrough advances in the past decades, Cu-mediated Ullmann-type cross-coupling reactions have been frequently implemented in academic research and have found ubiquitous industrial applications including the preparation of pharmaceutical and agrochemical products. This review provides an overview of selected general Cu-mediated Ullmann-type transformations for the formation of carbon− carbon and carbon−heteroatom (C−N, C−O, C−S, and C−P) bonds and their applications in route design, process development, and scale-up of pharmaceutical and agrochemical processes.

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“…Ultrasonic and microwave irradiation have been successfully utilised in the synthesis of N-arylanthranilic acids derivatives. 10,11 For example, Rolando and his co-workers 12 have studied the reaction of 2-chlorobenzoic acids and aminothiazoles or aminobenzothiazoles under ultrasonic irradiation using copper catalysis, and the results show that the yields were enhanced and the reaction time was reduced. Younis and his co-workers 13 used microwave irradiation to synthesise N-substituted 5-nitroanthranilic acid derivatives without a catalyst nor solvent and obtained yields up to 99% within 5−30 min at 80−120 °C.…”

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confidence: 99%

Metal Catalyst-Free Amination of 2-chloro-5-nitrobenzoic Acid in Superheated Water

Lan

Xia

et al. 2012

Journal of Chemical Research

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A series of N-arylanthranilic acid derivatives were synthesised by amination of 2-chloro-5-nitrobenzoic acid with various arylamine in superheated water with potassium carbonate as base. Good yields were achieved within 2−3 h at 150−190 °C. The results indicated that this metal catalyst-free method is a simple, environmentally-friendly and efficient synthesis of N-phenylanthranilic acid derivatives. Furthermore, it will work with an alkylamine and phenol.

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Fast Synthesis of Substituted N‐Phenylanthranilic Acids Using Ullmann Condensation Under Microwave Irradiation in Dry Media

Cited by 15 publications

References 3 publications

Synthesis of substituted diphenylamines and carbazoles: phototransformation products of diclofenac

Synthesis of substituted diphenylamines and carbazoles: phototransformation products of diclofenac

Cu-Mediated Ullmann-Type Cross-Coupling and Industrial Applications in Route Design, Process Development, and Scale-up of Pharmaceutical and Agrochemical Processes

Metal Catalyst-Free Amination of 2-chloro-5-nitrobenzoic Acid in Superheated Water

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