2054-16-2Relevant academic research and scientific papers
Amidation of aldehydes and alcohols through α-iminonitriles and a sequential oxidative three-component strecker reaction/thio-michael addition/alumina-promoted hydrolysis process to access β-mercaptoamides from aldehydes, amines, and thiols
Gualtierotti, Jean-Baptiste,Schumacher, Xavier,Fontaine, Patrice,Masson, Géraldine,Wang, Qian,Zhu, Jieping
supporting information, p. 14812 - 14819 (2013/01/15)
Mild and general alumina-promoted hydrolysis conditions for converting α-iminonitriles into carboxamides have been developed. In combination with the oxidative three-component Strecker reaction, the one-pot direct amidation of aldehydes and alcohols is reported. Subsequently, an Yb(OTf) 3-catalyzed Michael addition of thiols to α,β-unsaturated α-iminonitriles is reported for the synthesis of β-mercapto-α- iminonitriles. The successful integration of an oxidative Strecker reaction, thio-Michael addition, and neutral-alumina-promoted hydrolysis of β-mercapto-α-iminonitriles into a three-component one-pot process allowed us to develop the direct conversion of amines, aldehydes, and thiols into β-mercaptoamides. All of these procedures were applicable to aromatic and aliphatic amines and aldehydes. First direct: The direct amidation reactions of aldehydes and alcohols were performed in combination with the oxidative three-component synthesis of α-iminonitriles. In addition, β-mercaptoamides were readily accessed from α,β-unsaturated aldehydes, amines, and thiols by a sequential process that involved a three-component Strecker reaction, Yb(OTf)3-catalyzed thio-Michael addition, and hydrolysis of the resulting β-mercapto-α-iminonitriles (see scheme). Copyright
Construction of highly functional α-amino nitriles via a novel multicomponent tandem organocatalytic reaction: A facile access to α-methylene γ-lactams
Pan, Feng,Chen, Jian-Ming,Zhuang, Zhe,Fang, Yin-Zhi,Zhang, Sean Xiao-An,Liao, Wei-Wei
, p. 2214 - 2217 (2012/04/10)
The first tertiary amine-catalyzed multicomponent tandem Strecker-allylic-alkylation (SAA) reaction has been developed, which provides a facile access to functionalized α-amino nitriles, which could be readily converted into α-methylene-γ-butyrolactams. The Royal Society of Chemistry 2012.
