876353-79-6Relevant academic research and scientific papers
Regioselective Radical Arene Amination for the Concise Synthesis ofortho-Phenylenediamines
Gillespie, James E.,Morrill, Charlotte,Phipps, Robert J.
supporting information, p. 9355 - 9360 (2021/07/19)
The formation of arene C-N bonds directly from C-H bonds is of great importance and there has been rapid recent development of methods for achieving this through radical mechanisms, often involving reactiveN-centered radicals. A major challenge associated with these advances is that of regiocontrol, with mixtures of regioisomeric products obtained in most protocols, limiting broader utility. We have designed a system that utilizes attractive noncovalent interactions between an anionic substrate and an incoming radical cation in order to guide the latter to the areneorthoposition. The anionic substrate takes the form of a sulfamate-protected aniline and telescoped cleavage of the sulfamate group after amination leads directly toortho-phenylenediamines, key building blocks for a range of medicinally relevant diazoles. Our method can deliver both free amines and monoalkyl amines allowing access to unsymmetrical, selectively monoalkylated benzimidazoles and benzotriazoles. As well as providing concise access to valuableortho-phenylenediamines, this work demonstrates the potential for utilizing noncovalent interactions to control positional selectivity in radical reactions.
Efficient and expeditious chemoselective BOC protection of amines in catalyst and solvent-free media
Viswanadham, Balaga,Mahomed, Abdul S.,Friedrich, Holger B.,Singh, Sooboo
, p. 1355 - 1363 (2017/02/15)
A green and eco-friendly route for the almost quantitative BOC protection of a large variety of aliphatic and aromatic amines, amino acids, and amino alcohols is reported in catalyst and solvent-free media under mild reaction conditions. The products were confirmed by 1H, 13C NMR, IR spectroscopy, and in some cases, elemental analysis. This protocol does not require any water quenches, solvent separations, and purification steps, such as recrystallization and column chromatography.
Palladium-Catalyzed Decarboxylative Synthesis of Arylamines
Dai, Qipu,Li, Peihe,Ma, Nuannuan,Hu, Changwen
, p. 5560 - 5563 (2016/11/17)
A novel approach has been developed for the synthesis of arylamines via the palladium-catalyzed intramolecular decarboxylative coupling (IDC) of aroyloxycarbamates, obtained in situ by reacting aryl carboxylic acids with hydroxycarbamates. The reaction offers facile access to structurally diverse arylamines with the site-specific formation of the C(sp2)-N bond under mild conditions.
N-Protection of amines using pyridinium 2,2,2-trifluoroacetate ionic liquid as an efficient and reusable catalyst
Karimian, Somaye,Tajik, Hassan
, p. 218 - 220 (2014/02/14)
A simple, green, and efficient method for the N-tert-butoxycarbonylation of amines by pyridinium 2,2,2-trifluoroacetate ([Py][OTf]) as an efficient and reusable catalyst is reported. In general, electron donating groups on aryl group give rise to the higher yields than electron withdrawing groups. Clean reaction, short reaction times, high yields, reusability of catalyst, and easy preparation of it are some advantages of this work.
A mild and green method for the N-BOC protection of amines without assistant of catalyst under solvent-free conditions
Mojtahedi, Mohammad Majid,Niknejad, Nina,Veisi, Hojat
, p. 121 - 125 (2013/07/26)
A facile, green and versatile method for the Boc protection of amines has been developed by a treatment with (Boc)2O without any additive at room temperature. The method is general for the preparation of N-Boc derivatives of aliphatic (acyclic and cyclic), aromatic, and heteroaromatic amines; primary and secondary amines. The advantages of this method are green, simplicity, short reaction times and excellent yields.
Regioselective synthesis of the 1-bromo-4-phenyl-tetrahydro-7-amino- benzocyclohepten-6-one, a subnanomolar aminopeptidase-N/CD13 inhibitor
Al-Lakkis-Wehbe, Mira,Roux, Lionel,Charrier, Cédric,Alavi, Sarah,Le Nou?n, Didier,Defoin, Albert,Tarnus, Céline,Albrecht, Sébastien
experimental part, p. 6447 - 6455 (2012/08/28)
A regioselective synthesis of the title 1-bromo-4-phenyl-tetrahydro-7- amino-benzocyclohepten-6-one 2 has been pursued and develop in order to allow a large scale synthesis of this highly potent and selective APN inhibitor (K i 60 pM). The pivo
Cyclization-carbonylation-cyclization coupling reactions of N-propargylanilines and o-alkynylphenols with palladium(II)-bisoxazoline catalysts
Kusakabe, Taichi,Sekiyama, Emika,Ishino, Yukari,Motodate, Satoshi,Kato, Shigeki,Mochida, Tomoyuki,Kato, Keisuke
supporting information; experimental part, p. 1825 - 1832 (2012/07/30)
Cyclization-carbonylation-cyclization coupling reactions (CCC-coupling reactions) of N-propargylanilines and o-alkynylphenols catalyzed by (box)Pd(II) complexes afforded symmetrical bis(quinolin-3-yl) and bis(benzofuran-3-yl) ketones, respectively, in mod
