141903-88-0Relevant articles and documents
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.]
Nonconventional carbon additions to azomethines. Aryl amination/idoline synthesis by direct aryl radical addition to azomethine nitrogen
Johnston, Jeffrey N.,Plotkin, Michael A.,Viswanathan, Rajesh,Prabhakaran, Erode N.
, p. 1009 - 1011 (2007/10/03)
(matrix presented) The generality of a new method for aryl amination has been defined. Ketimines derived from o-bromophenethylamine cyclize to the N-substituted indoline when treated with nBu3SnH and a radical initiator. The pH-neutral conditions tolerate base- and acid-sensitive functionality. The observed regioselectivity is nonconventional for addition reactions involving carbon radicals and carbon-heteroatom π-bonds.
Nitrogen Transfer to Carbon Radicals
Barton, Derek H.R.,Jaszberenyi, Joseph Cs.,Theodorakis, Emmanouil A.
, p. 5904 - 5905 (2007/10/02)
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