Steroid-Derived Naphthoquinoline Asphaltene Model Compounds: Hydriodic Acid Is the Active Catalyst in I2-Promoted Multicomponent Cyclocondensation Reactions

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• 作者：Matthias Schulze ; David E. Scott ; Alexander Scherer ; Frank Hampel ; Robin J. Hamilton ; Murray R. Gray ; Rik R. Tykwinski ; Jeffrey M. Stryker
• 刊名：Organic Letters
• 出版年：2015
• 出版时间：December 4, 2015
• 年：2015
• 卷：17
• 期：23
• 页码：5930-5933
• 全文大小：301K
• ISSN：1523-7052

文摘

A multicomponent cyclocondensation reaction between 2-aminoanthracene, aromatic aldehydes, and 5-伪-cholestan-3-one has been used to synthesize model asphaltene compounds. The active catalyst for this reaction has been identified as hydriodic acid, which is formed in situ from the reaction of iodine with water, while iodine is not a catalyst under anhydrous conditions. The products, which contain a tetrahydro[4]helicene moiety, are optically active, and the stereochemical characteristics have been examined by VT-NMR and VT-CD spectroscopies, as well as X-ray crystallography.