20893-05-4Relevant academic research and scientific papers
PREPARATION OF SECONDARY AMINES WITH ELECTROPHILIC N-LINCHPIN REAGENTS
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Page/Page column 56; 58, (2018/12/13)
In one aspect, the present disclosure provides methods of preparing a secondary amine. In some embodiments, the secondary amine comprises two different groups or two identifical groups. Also provided herein are compositions for use in the preparation of the secondary amine.
Practical Singly and Doubly Electrophilic Aminating Agents: A New, More Sustainable Platform for Carbon-Nitrogen Bond Formation
Kattamuri, Padmanabha V.,Yin, Jun,Siriwongsup, Surached,Kwon, Doo-Hyun,Ess, Daniel H.,Li, Qun,Li, Guigen,Yousufuddin, Muhammed,Richardson, Paul F.,Sutton, Scott C.,Kürti, László
, p. 11184 - 11196 (2017/08/21)
Given the importance of amines in a large number of biologically active natural products, active pharmaceutical ingredients, agrochemicals, and functional materials, the development of efficient C-N bond-forming methods with wide substrate scope continues to be at the frontier of research in synthetic organic chemistry. Here, we present a general and fundamentally new synthetic approach for the direct, transition-metal-free preparation of symmetrical and unsymmetrical diaryl-, arylalkyl-, and dialkylamines that relies on the facile single or double addition of readily available C-nucleophiles to the nitrogen atom of bench-stable electrophilic aminating agents. Practical single and double polarity reversal (i.e., umpolung) of the nitrogen atom is achieved using sterically and electronically tunable ketomalonate-derived imines and oximes. Overall, this novel approach represents an operationally simple, scalable, and environmentally friendly alternative to transition-metal-catalyzed C-N cross-coupling methods that are currently used to access structurally diverse secondary amines.
Highly efficient sequential N,N,C-trialkylation of α-N-acyloxyimino esters
Mizota, Isao,Maeda, Tatsuya,Shimizu, Makoto
, p. 5793 - 5799 (2015/08/03)
α-N-Acyloxyimino esters serve as highly efficient substrates for the N,N,C-trialkylation reaction that can introduce various patterns of nucleophiles at the imino nitrogen and carbon atoms to synthesize N,N-dialkylated and N,N,C-trialkylated α-amino esters in moderate to high yields.
SYNTHESE DE 1,2,3-TRIAZOLINES PAR CYCLOADDITION DIPOLAIRE-1,3 DE DIAZOALCANES A DES ESTERS D'OXIMES
Perrocheau, J.,Carrie, R.
, p. 749 - 760 (2007/10/02)
Oximino-cyanacetic or malonesters 1, 2, 3 and 4 lead with diazoalcanes RCHN2 (R = H, CH3, Ph) to 1,2,3-triazolines.These triazolines present a low stability, however they are obtained crystallized with good yields.They are fully characterized and orientation of the cycloaddition is established.
1-ACYLOXYAZIRIDINE-2,2-DICARBOXYLIC ACID ESTERS
Mishchenko, A. I.,Prosyanik, V. A.,Belov, P. N.,Romanchenko, V. A.,Belova, E. G.,Markov, V. I.
, p. 270 - 274 (2007/10/02)
The reaction of diazomethane and O-acylisonitrosomalonates gave Δ2-1,2,3-triazoline-5,5-dicarboxylic acid esters, the rates of formation and thermal stabilities of which are determined by the character of this substituent attached to the oxygen
