697764-01-5Relevant academic research and scientific papers
Mechanistic Studies on the Michael Addition of Amines and Hydrazines to Nitrostyrenes: Nitroalkane Elimination via a Retro-aza-Henry-Type Process
Kallitsakis, Michael G.,Tancini, Peter D.,Dixit, Mudit,Mpourmpakis, Giannis,Lykakis, Ioannis N.
, p. 1176 - 1184 (2018/02/09)
In this article we report on the mechanistic studies of the Michael addition of amines and hydrazines to nitrostyrenes. Under the present conditions, the corresponding N-alkyl/aryl substituted benzyl imines and N-methyl/phenyl substituted benzyl hydrazones were observed via a retro-aza-Henry-type process. By combining organic synthesis and characterization experiments with computational chemistry calculations, we reveal that this reaction proceeds via a protic solvent-mediated mechanism. Experiments in deuterated methanol CD3OD reveal the synthesis and isolation of the corresponding deuterated intermediated Michael adduct, results that support the proposed slovent-mediated pathway. From the synthetic point of view, the reaction occurs under mild, noncatalytic conditions and can be used as a useful platform to yield the biologically important N-methyl pyrazoles in a one-pot manner, simple starting with the corresponding nitrostyrenes and the methylhydrazine.
Cobalt-catalyzed acceptorless alcohol dehydrogenation: Synthesis of imines from alcohols and amines
Zhang, Guoqi,Hanson, Susan K.
supporting information, p. 650 - 653 (2013/04/11)
A cobalt catalyst has been developed for the acceptorless dehydrogenation of alcohols and applied to synthesize imines from alcohols and amines. Deuterium labeling studies suggest that the reaction proceeds by an initial reversible alcohol dehydrogenation step involving a cobalt hydride intermediate.
