7173-86-6Relevant articles and documents
Tunable Synthesis of α-Amino Boronic Esters from Available Aldehydes and Amines through Sequential One-Pot Dehydration and Copper-Catalyzed Borylacylation
Xia, Qi,Chang, Hua-Rong,Li, Juan,Wang, Jia-Yi,Peng, Yan-Qing,Song, Gong-Hua
, p. 2716 - 2724 (2020/01/31)
Copper-catalyzed multicomponent borylacylation of imines with acid chlorides and bis(pinacolato)diboron was developed for the preparation of synthetically useful and pharmacologically relevant α-amino boronic acid derivatives. Starting from a range of acid chlorides and imines with aryl, heteroaryl, and alkyl substituents, most of these ligand-free reactions proceeded smoothly at room temperature in moderate to good yields. Furthermore, a facile and convenient one-pot, multistep access to the direct synthesis of α-amino boronic acid derivatives from available aldehydes and amines was also developed.
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.
Integrative Theory/Experiment-Driven Exploration of a Multicomponent Reaction towards Imidazoline-2-(thi)ones
Kruithof, Art,Mulder, Jos R.,Ruiz,Janssen, Elwin,Mooijman,Ruijter, Eelco,Fonseca Guerra, Célia,Bickelhaupt, F. Matthias,Orru, Romano V. A.
supporting information, p. 104 - 112 (2018/01/17)
Predicting reactivity in multicomponent reactions (MCRs) is extremely difficult. These reactions proceed by multiple pathways and are inherently associated with a potentially large variation of reactants and functional groups. To date, theoretical chemist
