Synthesis and characterization of steroidal, anellated aminothiophenes by Gewald reaction

Oliver Kraft, G. Mittag, Sophie Hoenke, Niels V. Heise, A. Al‐Harrasi, R. Csuk
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Abstract

Gewald 3-component reactions (G-3CR), i.e., reactions of a carbonyl compound with an activated nitrile in the presence of a secondary amine and sulfur, lead straightforwardly to anellated 2-aminothiophenes. Interestingly, their application to steroidal hydrocarbons has been limited to a single example. We could show in this work that Gewald 3-component reactions can be performed successfully for molecules holding a cholesterol or sitostanol skeleton, such as 5a-cholestan3-one (8) and 5a-sitostan-3-one (11), thus leading in good yields to the corresponding anellated steroidal 2-amino-thiophenes 12-15. Gewald reaction proved to be an excellent method to access heterocyclic steroids.
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格瓦尔德反应合成甾体氨基噻吩及其表征
格瓦尔德三组分反应(G-3CR),即羰基化合物与活性腈在仲胺和硫存在下的反应,直接导致2-氨基噻吩。有趣的是,它们在甾体烃上的应用仅限于一个例子。我们可以在这项工作中证明,对于含有胆固醇或谷甾醇骨架的分子,如5a-胆甾醇-3-one(8)和5a-谷甾醇-3-one(11),可以成功地进行Gewald 3组分反应,从而产生相应的甾体2-氨基噻吩12-15。格瓦尔德反应被证明是获得杂环甾体的一种很好的方法。
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