2717-75-1Relevant academic research and scientific papers
Iron-catalyzed oxidative amidation of acylhydrazines with amines
Wang, Yi-Jie,Zhang, Guo-Yu,Shoberu, Adedamola,Zou, Jian-Ping
, (2021/08/18)
A new approach for amide bond formation via a mild and efficient Iron-catalyzed cross-coupling reaction of acylhydrazines and amines using TBHP as oxidant is described. This protocol is compatible with a wide range of amines and acylhydrazines. In addition, the synthetic application of the reaction is presented.
Tris(o-phenylenedioxy)cyclotriphosphazene as a Promoter for the Formation of Amide Bonds between Aromatic Acids and Amines
Movahed, Farzaneh Soleymani,Sawant, Dinesh N.,Bagal, Dattatraya B.,Saito, Susumu
, p. 3253 - 3262 (2020/11/02)
The atom-efficient formation of amide bonds has emerged as a top-priority research field in organic synthesis, as amide bonds constitute the backbones of proteins and represent an important structural motif in drug molecules. Currently, the increasing demand for novel discoveries in this field has focused substantial attention on this challenging subject. Herein, the degradable 1,3,5-triazo-2,4,6-triphosphorine (TAP) motif is presented as a new condensation system for the dehydrative formation of amide bonds between diverse combinations of aromatic carboxylic acids and amines. The underlying reaction mechanism was investigated, and potential catalyst intermediates were characterized using 31 P NMR spectroscopy and ESI mass spectrometry.
Diboron-Catalyzed Dehydrative Amidation of Aromatic Carboxylic Acids with Amines
Sawant, Dinesh N.,Bagal, Dattatraya B.,Ogawa, Saeko,Selvam, Kaliyamoorthy,Saito, Susumu
supporting information, p. 4397 - 4400 (2018/08/09)
Tetrakis(dimethylamido)diboron and tetrahydroxydiboron are herein reported as new catalysts for the synthesis of aryl amides by catalytic condensation of aromatic carboxylic acids with amines. The developed protocol is both simple and highly efficient over a broad range of substrates. This method thus represents an attractive approach for the use of diboron catalysts in the synthesis of amides without having to resort to stoichiometric or additional dehydrating agents.
Design, synthesis, and molecular docking studies of N-(9,10-anthraquinone-2-carbonyl)amino acid derivatives as xanthine oxidase inhibitors
Zhang, Ting-Jian,Li, Song-Ye,Yuan, Wei-Yan,Zhang, Yi,Meng, Fan-Hao
, p. 893 - 901 (2018/03/21)
A series of N-(9,10-anthraquinone-2-carbonyl)amino acid derivatives (1a–j) was designed and synthesized as novel xanthine oxidase inhibitors. Among them, the L/D-phenylalanine derivatives (1d and 1i) and the L/D-tryptophan derivatives (1e and 1j) were effective with micromolar level potency. In particular, the L-phenylalanine derivative 1d (IC50?=?3.0?μm) and the D-phenylalanine derivative 1i (IC50?=?2.9?μm) presented the highest potency and were both more potent than the positive control allopurinol (IC50?=?8.1?μm). Preliminary SAR analysis pointed that an aromatic amino acid fragment, for example, phenylalanine or tryptophan, was essential for the inhibition; the D-amino acid derivative presented equal or greater potency compared to its L-enantiomer; and the 9,10-anthraquinone moiety was welcome for the inhibition. Molecular simulations provided rational binding models for compounds 1d and 1i in the xanthine oxidase active pocket. As a result, compounds 1d and 1i could be promising lead compounds for further investigation.
Peptide-catalyzed conversion of racemic oxazol-5(4 H)-ones into enantiomerically enriched α-amino acid derivatives
Metrano, Anthony J.,Miller, Scott J.
, p. 1542 - 1554 (2014/03/21)
We report the development and optimization of a tetrapeptide that catalyzes the methanolytic dynamic kinetic resolution of oxazol-5(4H)-ones (azlactones) with high levels of enantioinduction. Oxazolones possessing benzylic-type substituents were found to perform better than others, providing methyl ester products in 88:12 to 98:2 er. The mechanism of this peptide-catalyzed process was investigated through truncation studies and competition experiments. High-field NOESY analysis was performed to elucidate the solution-phase structure of the peptide, and we present a plausible model for catalysis.
Dynamic kinetic resolution: Synthesis of optically active α-amino acid derivatives
Brown, Stuart A.,Parker, Marie-Claire,Turner, Nicholas J.
, p. 1687 - 1690 (2007/10/03)
Candida antarctica lipase B (Novozyme) is an effective catalyst for the dynamic kinetic resolution of racemic 2-benzyl-4-substituted-5(4H)- oxazolones, in the presence of an alcohol, yielding optically active N- benzoyl amino acid esters. The reaction has been optimised with respect to the solvent and the effect of a catalytic amount of organic base is investigated. (C) 2000 Elsevier Science Ltd.
New methodology for high throughput solution-phase synthesis: Affinity purification by using crown ether and ammonium ion interaction
Zhang, San-qi,Fukase, Koichi,Kusumoto, Shoichi
, p. 7479 - 7483 (2007/10/03)
A new method for affinity purification of synthetic compounds by using crown ether-ammonium ion interaction and its application to the synthesis of several peptides and heterocycles are described. The desired compounds possessing the crown ether (32-crown
CONSTRUCTION OF OPTICALLY PURE TRYPTOPHANS FROM SERINE DERIVED AZIRIDINE-2-CARBOXYLATES
Sato, Kazuo,Kozikowski, Alan P.
, p. 4073 - 4076 (2007/10/02)
The possibility of preparing optically pure tryptophan derivatives from various substituted indoles and (2R)- or (2S)-2-aziridinecarboxylates has been examined.Zinc triflate was found to be the only Lewis acid capable of bringing about this reaction in mo
Electroorganic Chemistry. 81. Anodic Oxidation of Sulfonamides and Amidophosphates
Shono, Tatsuya,Matsumura, Yoshihiro,Tsubata, Kenji,Uchida, Kenshi,Kanazawa, Takenobu,Tsuda, Kunio
, p. 3711 - 3716 (2007/10/02)
Oxidation peak potentials of sulfonamides and amidophosphates were measured in acetonitrile and compared with the corresponding amides and carbamates.The results showed that the order of easiness of oxidation was amides > carbamates > amidophosphates > sulfonamides.Furthermore, the reaction of silyl enol ethers or trimethyl phosphite with anodically α-methoxylated sulfonamides or amidophosphates has clearly shown that the α-methoxylated compounds are useful starting materials in organic synthesis.For example, optically active L-tryptophan was synthesized from α-methoxylated N-(p-tolylsulfonyl)-L-proline ester.
Synthesis of Oxazolylindole Alkaloids from Tryptamine and Tryptophan by Oxidation with 2,3-Dichloro-5,6-dicyanobenzoquinone
Yoshioka, Tadao,Mohri, Kunihiko,Oikawa, Yuji,Yonemitsu, Osamu
, p. 2252 - 2281 (2007/10/02)
When N-acyl derivatives of tryptamine and L-tryptophan methyl ester were treated with DDQ (2 equiv) in tetrahydrofuran or other anhydrous solvents, four consecutive reactions, dehydrogenation, nucleophilic cyclization, another dehydrogenation, and isomeri
