Isolation and characterization of human urinary metabolites of meclomen.

Matsuki, Yasuhiko; Dan, Junko; Fukuhara, Katsuharu; Ito, Tomiharu; Nambara, Toshio

doi:10.1248/cpb.36.1431

Cited by 6 publications

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“…Aminophenols constitute a common structural motif in various potentially useful therapeutic agents and drug candidates . The similarity in conditions between N -arylation and O -arylation suggested that the present protocol could be used as a tandem reaction, and this was indeed the case (Scheme ).…”

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confidence: 64%

CuI-Nanoparticles-Catalyzed Selective Synthesis of Phenols, Anilines, and Thiophenols from Aryl Halides in Aqueous Solution

et al. 2011

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confidence: 64%

CuI-Nanoparticles-Catalyzed Selective Synthesis of Phenols, Anilines, and Thiophenols from Aryl Halides in Aqueous Solution

et al. 2011

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“…13 O-or N-arylated aminophenol products constitute a common structural motif in various potentially useful therapeutic agents and/or drug candidates (Figure 1). [14][15][16][17][18][19][20][21][22] They have also been applied as building blocks for the preparation of organic materials. 23 We were interested in developing a catalytic system capable of selectively arylating either the nitrogen or the oxygen of the different isomers of aminophenols.…”

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confidence: 99%

Orthogonal Cu- and Pd-Based Catalyst Systems for the O- and N-Arylation of Aminophenols

2009

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O-or N-arylated aminophenol products constitute a common structural motif in various potentially useful therapeutic agents and/or drug candidates. We have developed a complementary set of Cu-and Pd-based catalyst systems for the selective O-and N-arylation of unprotected aminophenols using aryl halides. Selective O-arylation of 3-and 4-aminophenols is achieved with copper-catalyzed methods employing picolinic acid or CyDMEDA, trans-N,N′-dimethyl-1,2-cyclohexanediamine, respectively, as the ligand. The selective formation of N-arylated products of 3-and 4-aminophenols can be obtained with BrettPhos precatalyst, a biarylmonophosphine-based palladium catalyst. 2-Aminophenol can be selectively N-arylated with CuI, although no system for the selective O-arylation could be found. Coupling partners with diverse electronic properties and a variety of functional groups can be selectively transformed under these conditions.

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Dialkylterphenyl Phosphine‐Based Palladium Precatalysts for Efficient Aryl Amination of N‐Nucleophiles

Rama

Maya

Nicasio

2020

Chemistry A European J

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Aseries of 2-aminobiphenyl palladacycles supported by dialkylterphenyl phosphines, PR 2 Ar' (R = Me, Et, iPr, Cyp (cyclopentyl), Ar' = Ar Dipp2 ,A r Xyl2f ,D ipp (2,6-C6H3-(2,6-C6H3-(CHMe2)2)2), Xyl = xylyl) have been prepareda nd structurally characterized. Neutral palladacycles were obtained with less bulky terphenyl phosphines (i.e.,M ea nd Et substituents) whereas the largest phosphines provided cationic palladacycles in whicht he phosphines adopted ab identate hemilabile k 1 -P,h 1 -C arene coordination mode.T he influence of the ligand structure on the catalytic performance of these Pd precatalysts was evaluated in aryl aminationr eactions.C ationicc omplexes bearing the phosphines Pi-Pr 2 Ar Xyl2 andP Cyp 2 Ar Xyl2 weret he most active of the series. Thesep recatalysts have demonstrated ah igh versatility and efficiency in the coupling of av ariety of nitrogen nucleophiles, including secondary amines, alkyl amines,a nilines, and indoles, with electronically deactivated and ortho-substituted aryl chloridesa tl ow catalyst loadings (0.25-0.75 mol % Pd) and withoutexcess ligand.[a] R.Supporting information and the ORCID identification number(s) for the author(s) of this article can be found under: https://doi.Scheme2.Synthesis of complexes 2a and 2b.Scheme3.Generalsynthesis of complexes 3d and 3e.

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Isolation and characterization of human urinary metabolites of meclomen.

Cited by 6 publications

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CuI-Nanoparticles-Catalyzed Selective Synthesis of Phenols, Anilines, and Thiophenols from Aryl Halides in Aqueous Solution

CuI-Nanoparticles-Catalyzed Selective Synthesis of Phenols, Anilines, and Thiophenols from Aryl Halides in Aqueous Solution

Orthogonal Cu- and Pd-Based Catalyst Systems for the O- and N-Arylation of Aminophenols

Dialkylterphenyl Phosphine‐Based Palladium Precatalysts for Efficient Aryl Amination of N‐Nucleophiles

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