Convenient Access to Substituted Acridines by a Buchwald—Hartwig Amination.

Abstract

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Development of Potent and Selective Inhibitors of Aldo–Keto Reductase 1C3 (Type 5 17β-Hydroxysteroid Dehydrogenase) Based on N-Phenyl-Aminobenzoates and Their Structure–Activity Relationships

“…All compounds were synthesized via a two-step reaction involving a Buchwald–Hartwig C–N coupling followed by saponification of the formed methyl ester (Scheme ). − Step A: Briefly, the aniline (1.2 equiv), Cs 2 CO 3 (1.4 equiv), BINAP (0.08 equiv), and Pd­(OAc) 2 (0.05 equiv) were added to a solution of the aryl bromide (or triflate) (1 equiv) in toluene (0.1 M) at room temperature. The reaction mixture was allowed to stir at 120 °C for 4–48 h. Once the reaction appeared to be complete by consumption of the bromide (or triflate) by TLC analysis, the mixture was allowed to cool to room temperature, diluted with EtOAc, washed with 2 M aq HCl (2×), brine, and dried over sodium sulfate.…”

Exploring Anti-Prion Glyco-Based and Aromatic Scaffolds: A Chemical Strategy for the Quality of Life

“…For the synthesis of quinacrine and their analogs, the corresponding anthranilic acids are used as starting materials by applying Ullmann-Jourdan reaction or Buchwald Hartwig amination [ 50 ] ( Scheme 8 ). Copper-catalyzed Ullmann–Jourdan reaction [ 51 ] is applied to substituted 2-chlorobenzoic acids and the corresponding aniline derivatives yielding the anthranilic acids in moderate yields.…”

“…Using a palladium-catalyzed Buchwald–Hartwig amination seems to be a more robust method for the synthesis of anthranilic acids. Reaction of methyl 2-iodobenzoates and anilines using Pd(ac) 2 , bis-[2-diphenylphosphino)phenyl]ether (DPEPhos) and Cs 2 CO 3 as base, and subsequent hydrolysis gave the corresponding acids [ 50 ] ( Scheme 8 ).…”

Studies directed towards nonyl acridine orange analogues having the potential to act as FRET donors with the PDT drug Pc 4

“…Under H 2 , a suspension of 12 (958 mg), Pd/C (10%) and CH 3 OH (50 mL) was stirred at room temperature for 2 days, ltered, and evaporated to an oil by rotary evaporation (room temperature). The oil was subjected to vacuum (40 C) and weighed (759 mg, 94% [22][23][24] a suspension of aniline 13 (1.32 g), 2-chloro-4-nitrobenzoic acid (829 mg), potassium carbonate (770 mg), copper powder (66 mg) and 1-pentanol (5 mL) was heated (reux) for 4.5 h, subjected to steam distillation and ltered. At 80-100 C, the ltrate was treated with aqueous HCl (2 N) until the pH was 4, ltered, allowed to stand overnight, and reltered.…”