Microwave-Promoted synthesis of novel N-Arylanthranilic acids

Abstract

Nesse trabalho é relatada a síntese de uma série de ácidos N-aril antranílicos inéditos, com bons a excelentes rendimentos, empregando irradiação de microondas como fonte de aquecimento para promover a reação de acoplamento de Ullmann entre ácidos antranílicos e brometos de arila contendo grupos substituintes doadores ou aceptores de elétrons.In this paper we report the synthesis of a series of novel N-aryl anthranilic acids, with good to excellent yields, employing microwaves as heat source to promote the Ullmann coupling between anthranilic acids and aryl bromides possessing electron donating or withdrawing groups.

Design, Synthesis and Characterization of Aurone Based α,β‐unsaturated Carbonyl‐Amino Ligands and their Application in Microwave Assisted Suzuki, Heck and Buchwald Reactions

“…2‐((4‐methoxyphenyl)amino)‐5‐nitrobenzoic acid (13 q) : [71] Light Yellow Solid; Yield 91%; m. p 231–232 °C; 1 H NMR (400 MHz, CDCl 3 +DMSO‐d 6 ) δ 10.04 (s, 1H), 8.70 (s, 1H), 7.86 (d, J =9.4 Hz, 1H), 6.98 (d, J =8.3 Hz, 2H), 6.76 (d, J =8.3 Hz, 2H), 6.68 (d, J =9.4 Hz, 1H), 3.64 (s, 3H); 13 C NMR (100 MHz, CDCl 3 +DMSO‐d 6 ) δ 169.61, 157.91, 154.09, 136.56, 130.97, 129.51, 129.05, 126.70, 114.93, 112.54, 110.18, 55.50.…”

Mild Copper-Catalyzed, l-Proline-Promoted Cross-Coupling of Methyl 3-Amino-1-benzothiophene-2-carboxylate

“…Many methods have been developed for the synthesis of anthranilic acids. Coppercatalyzed arylation is one of the most powerful tools for the synthesis of N-arylanthranilic acids, which are important precursors for the synthesis of substituted acridines and acridones [22][23][24][25][26][27]. Many methods have been developed for the synthesis of anthranilic acids.…”

Microwave-assisted synthesis of Nitroketene N,S-Arylaminoacetals

“…Clearly, reductions in reaction times, improved yields and suppression of side products, relative to conventional thermal heating, are some benefits of this emerging technology. [13][14][15] In this paper we report the use of microwaves as heat source to promote the synthesis of a series of nitroketene N,S-acetals with good to excellent isolated yields.…”