硫代酸介导的叠氮化物向酰胺的转化——通往奥罗定生物碱的探索性研究。
Thio acid-mediated conversion of azides to amides - exploratory studies en route to oroidin alkaloids.
作者信息
Herath Apsara K, Bhandari Manoj R, Gout Delphine, Yousufuddin Muhammed, Lovely Carl J
机构信息
Department of Chemistry and Biochemistry, 700 Planetarium Place, University of Texas at Arlington, TX 76019, USA.
Life and Health Sciences Department, 7400 University Hills Blvd, University of North Texas at Dallas, Dallas, TX 75241, USA.
出版信息
Tetrahedron Lett. 2017 Oct 11;58(41):3913-3918. doi: 10.1016/j.tetlet.2017.08.050. Epub 2017 Aug 24.
Abstract
The utility of the thio acid-azide coupling reaction to afford amides is explored in imidazole-containing substrates for application in the total synthesis of examples of oroidin alkaloids. Good yields of the expected amides are obtained in both monomeric and dimeric substrates. Bis azides react preferentially at the 2-azido position but hydrosulfenylation and reduction interfere. 2-Thiophenyl and 2-oxo groups were evaluated as 2-amino surrogates, the thioether delivered the expected amide, whereas 2-imidazolone gave a mixture of the expected amide and the hydrosulfenylation product.
摘要
研究了硫代酸-叠氮偶联反应在含咪唑底物中制备酰胺的实用性，以用于奥罗定生物碱实例的全合成。在单体和二聚体底物中均获得了预期酰胺的良好产率。双叠氮化物优先在2-叠氮基位置反应，但氢硫基化和还原会产生干扰。评估了2-硫代苯基和2-氧代基团作为2-氨基替代物，硫醚得到了预期的酰胺，而2-咪唑酮得到了预期酰胺和氢硫基化产物的混合物。
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