23535-28-6Relevant academic research and scientific papers
Electrochemical Oxidative Coupling between Benzylic C(sp3)-H and N-H of Secondary Amines: Rapid Synthesis of α-Amino α-Aryl Esters
Chauhan, Pankaj,Choudhary, Rahul,Kumar, Indresh,Nagare, Yadav Kacharu,Pawar, Amol Prakash,Shah, Imtiyaz Ahmad,Yadav, Jyothi
, p. 9682 - 9691 (2021/07/26)
An intermolecular electrochemical coupling between the benzylic C(sp3)-H bond and various secondary amines is reported. The electronic behavior of two electronically rich units viz the α-position of α-aryl acetates and amines was engineered electrochemically, thus facilitating their reactivity for the direct access of α-amino esters. A series of acyclic/cyclic secondary amines and α-aryl acetates were tested to furnish the corresponding α-amino esters with high yields (up to 92%) under mild conditions.
Tandem N, N-Dialkylation Reaction of N-Trimethylsilyl α-Iminoesters Utilizing an Umpolung Reaction and Characteristics of the Silyl Substituent: Synthesis of Pyrrolidine, Piperidine, and Iminodiacetate
Mizota, Isao,Tadano, Yurie,Nakamura, Yusuke,Haramiishi, Tomoki,Hotta, Miyuki,Shimizu, Makoto
, p. 2663 - 2667 (2019/04/30)
Umpolung reactions of N-trimethylsilyl α-iminoester with organometallics gave directly N-alkylaminoesters in high yields without the need for removing a protecting group at the nitrogen atom. Efficient syntheses of pyrrolidines, piperidines, and iminodiacetate derivatives were also developed via tandem N,N- or N,C-dialkylation reactions utilizing characteristics of the silyl substituent. Furthermore, under the influence of silica gel, the addition of an enolate to the imino nitrogen proceeded to give an iminodiacetate derivative.
Enantioselective Palladium-Catalyzed Carbene Insertion into the N?H Bonds of Aromatic Heterocycles
Arredondo, Vanessa,Hiew, Stanley C.,Gutman, Eugene S.,Premachandra, Ilandari Dewage Udara Anulal,Van Vranken, David L.
, p. 4156 - 4159 (2017/04/03)
C3-substituted indoles and carbazoles react with α-aryl-α-diazoesters under palladium catalysis to form α-(N-indolyl)-α-arylesters and α-(N-carbazolyl)-α-arylesters. The products result from insertion of a palladium-carbene ligand into the N?H bond of the aromatic N-heterocycles. Enantioselection was achieved using a chiral bis(oxazoline) ligand, in many cases with high enantioselectivity (up to 99 % ee). The method was applied to synthesize the core of a bioactive carbazole derivative in a concise manner.
Copper(I)-catalyzed coupling reaction of aryl boronic acids with N,O-acetals and N,N-aminals under atmosphere leading to α-aryl glycine derivatives and diarylmethylamine derivatives
Sakai, Norio,Hori, Hiroaki,Yoshida, Yoshihiro,Konakahara, Takeo,Ogiwara, Yohei
, p. 4722 - 4729 (2015/07/27)
We demonstrated a copper(I)-catalyzed coupling reaction of aryl boronic acids with N,O-acetals and N,N-aminals leading to the synthesis of α-aryl glycines and diarylmethylamines. Under an ambient atmosphere, this catalytic system could be applied to the activation of a C(sp3)-O bond of N,O-acetals with an ester and an aryl group, or without a coordinating substituent, as well as to a C(sp3)-N bond of N,N-aminals.
Synthesis and characterization of bisoxazolines- and pybox-copper(II) complexes and their application in the coupling of α-carbonyls with functionalized amines
Jia, Wei-Guo,Li, Dan-Dan,Dai, Yuan-Chen,Zhang, Hui,Yan, Li-Qin,Sheng, En-Hong,Wei, Yun,Mu, Xiao-Long,Huang, Kuo-Wei
supporting information, p. 5509 - 5516 (2014/07/21)
Binuclear complexes [{(DMOX)CuCl}2(μ-Cl)2] (1), mononuclear complexes [(DMOX)CuBr2] (2) (DMOX = 4,5-dihydro-2-(4,5- dihydro-4,4-dimethyloxazol-2-yl)-4,4-dimethyloxazole) and the pybox Cu(ii) complex [(Dm-Pybox)CuBr2/
Copper-catalyzed amination of silyl ketene acetals with N-chloroamines
Miura, Tomoya,Morimoto, Masao,Murakami, Masahiro
, p. 5214 - 5217,4 (2020/09/02)
A copper(I)/2,2′-bipyridyl complex catalyzes an amination reaction of silyl ketene acetals with N-chloroamines, presenting a new preparative method of α-amino esters.
A formal method for the de-N,N-dialkylation of Sommelet-Hauser rearrangement products
Tayama, Eiji,Sato, Ryota,Takedachi, Keisuke,Iwamoto, Hajime,Hasegawa, Eietsu
supporting information; experimental part, p. 4710 - 4718 (2012/07/28)
Selective amine de-alkylation enables the conversion of Sommelet-Hauser rearrangement products into 2-aryl-2-bromoacetic acid derivatives. These compounds are valuable synthetic intermediates in the synthesis of α-aryl-α-amino or α-aryl-β-amino acid deriv
Novel analogues of ketamine and phencyclidine as NMDA receptor antagonists
Zarantonello, Paola,Bettini, Ezio,Paio, Alfredo,Simoncelli, Chiara,Terreni, Silvia,Cardullo, Francesco
scheme or table, p. 2059 - 2063 (2011/04/24)
The identification of structurally novel analogues of ketamine and phencyclidine (PCP), as NMDA receptor antagonists, with low to moderate potency at GluN2A and GluN2B receptors is discussed. In particular, some examples, such as compounds 6 and 10, shows decreased calculated lipophilicity, when compared to PCP, while retaining moderate activity. Moreover, the germinal aryl amino substituted lactam ring, as exemplified in compounds 7-10 and 11-13, constitutes a novel scaffold with potential application in the design of biologically active compounds.
Discovery of triarylethanolamine inhibitors of the Kv1.5 potassium channel
Beshore, Douglas C.,Liverton, Nigel J.,McIntyre, Charles J.,Claiborne, Christopher F.,Libby, Brian,Culberson, J. Christopher,Salata, Joseph J.,Regan, Christopher P.,Lynch, Joseph J.,Kiss, Laszlo,Spencer, Robert H.,Kane, Stephanie A.,White, Rebecca B.,Yeh, Suzie,Hartman, George D.,Dinsmore, Christopher J.
scheme or table, p. 2493 - 2496 (2010/08/06)
A series of triarylethanolamine inhibitors of the Kv1.5 potassium channel have been prepared and evaluated for their effects in vitro and in vivo. The structure-activity relationship (SAR) studies described herein led to the development of potent, selecti
A NOVEL 4-METHYLBENZENESULPHONATE SALT AND A PROCESS FOR PREPARING A PHARMACEUTICAL COMPOSITION COMPRISING THE SALT
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Page/Page column 27, (2010/12/29)
The invention provides a 4-methylbenzenesulphonate salt of the muscarinic antagonist (R)- 1-(4-fluorophenethyl)-3-((S)-2-phenyl-2-(piperidin-1 -yl)propanoyloxy)-1- azoniabicyclo[2.2.2]octane and its use in therapy,as well as a process for preparing a pharmaceutical composition comprising the salt and its use in therapy.
