84452-37-9Relevant academic research and scientific papers
Photocatalytic divergent decarboxylative amination: a metal-free access to aliphatic amines and hydrazines
Shu, Xianli,Xu, Ruting,Liao, Saihu
, p. 1756 - 1762 (2021/09/06)
Nitrogen-containing motifs are widely present in natural products, bioactive molecules, and drugs. Accordingly, effective synthetic methods with high efficiency and diversity are highly desirable. Here, we present the invention of a facile, visible light-mediated decarboxylative C(sp3)-N bond-forming reaction by employing abundant carboxylic acids as the feedstock and a commercial diazirine as a nitrogen donor. This process is amenable to access both imines and diaziridines, as the corresponding masked amines and hydrazines, through a selectable single or double nitrogen transfer from the diazirine, respectively. This divergent approach works well in both directions with various alkyl carboxylic acids, including primary, secondary, and tertiary acids, as well as natural products and drugs, thus affording a rapid, metal-free approach to build nitrogen-containing molecule libraries with considerable structural diversity, which could thus benefit the related study in context of chemical biology and drug discovery. [Figure not available: see fulltext.]
The invention of radical reactions. 30. Diazirines as carbon radical traps. Mechanistic aspects and synthetic applications of a novel and efficient amination process
Barton, Derek H. R.,Jaszberenyi, Joseph Cs.,Theodorakis, Emmanouil A.,Reibenspies
, p. 8050 - 8059 (2007/10/02)
A number of diazirines were synthesized for the purpose of exploring the addition of a carbon radical to the nitrogen-nitrogen double bond. Carbon radicals, generated from the photolysis of the O-acyl derivatives of N-hydroxy-2-thiopyridone or via radical exchange from the corresponding organotellurides, were shown to add smoothly to the diazirines leading to imines 34. When 3-(trifluoromethyl)-3-phenyldiazirine (13) is used as the trap, the thus formed imines can be easily hydrolyzed to amines. A mechanism that involves dimerization of the diaziridinyl radicals 32 to produce tetraazo intermediates 33 is suggested in accord with variable temperature NMR data for the reaction. Proof for this mechanistic scheme was furthermore obtained by isolation and X-ray structure determination of 33d. The first X-ray structure of a 3-(trifluoromethyl)-3-aryldiazirine is also reported.
N,N'-BIS(1-CHLOROALKYL)CARBODIIMIDES. II. REACTIONS WITH PROTON-CONTAINING NUCLEOPHILIC REAGENTS
Fetyukhin, V. N.,Vovk, M. V.,Pirozhenko, V. V.,Samarai, L. I.
, p. 1822 - 1828 (2007/10/02)
The reactions of N,N'-bis(1-chloroalkyl)carbodiimides with proton-containing nucleophilic reagents were investigated.It was shown that substitution products retaining the carbodiimide structure are formed in the reactions with alcohols and phenols.The action of water or primary amines is accompanied by fragmentation of the molecule and leads to the production of chloroformamidine or N-substituted guanidines.Secondary amines act on N,N'-bis(1-chloroalkyl)carbodiimides to form diazadienes, which exist as mixtures of Z,E isomers.
