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首页> 外文期刊>Chemistry: A European journal >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
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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

机译：醛和醇通过α-亚胺的酰胺化反应和顺序氧化三组分strecker反应/硫代迈克尔加成反应/氧化铝促进的水解过程，以从醛，胺和硫醇中获得β-巯基酰胺

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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).
机译：已经开发了温和且一般的氧化铝促进的水解条件，用于将α-亚氨基腈转化为羧酰胺。与氧化性三组分斯特雷克反应结合，报道了醛和醇的一锅直接酰胺化。随后，据报道Yb（OTf）_3催化硫醇向α，β-不饱和α-亚腈的迈克尔加成反应，从而合成了β-巯基-α-亚腈。氧化斯特雷克反应，硫代迈克尔加成反应和中性氧化铝促进的β-巯基-α-亚甲基腈水解成功整合为三组分一锅法，使我们得以开发胺，醛，和硫醇成β-巯基酰胺所有这些程序均适用于芳族和脂族胺和醛。第一次直接：将醛和醇的直接酰胺化反应与α-亚胺的氧化三组分合成结合进行。此外，通过涉及三组分Strecker反应，Yb（OTf）_3催化的硫代迈克尔基加成反应和水解反应的顺序过程，很容易从α，β-不饱和醛，胺和硫醇中获得β-巯基酰胺。生成的β-巯基-α-亚腈（参见方案）。

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