新型三环化学类型的简洁制备：稠合乙内酰脲 - 苯二氮䓬类化合物
Concise Preparation of Novel Tricyclic Chemotypes: Fused Hydantoin-benzodiazepines.
作者信息
Gunawan Steven, Nichol Gary S, Chappeta Shashi, Dietrich Justin, Hulme Christopher
机构信息
The Southwest Comprehensive Center for Drug Discovery and Development, College of Pharmacy, Department of Pharmacology/Toxicology, The University of Arizona, Tucson, AZ 85721.
出版信息
Tetrahedron Lett. 2010 Sep 8;51(36):4689-4692. doi: 10.1016/j.tetlet.2010.06.131.
Abstract
The following article describes a concise synthesis of a collection of 4,5-dihydro-1H-benzo[e][1,4]diazepines fused to a hydantoin ring. Molecular complexity and biological relevance is high and structures are generated in a mere three steps, employing the Ugi reaction to assemble diversity reagents. The protocol represents a novel UDC (Ugi-deprotect-cyclize) strategy employed in the Ugi-5-component CO(2) mediated condensation, followed by further cyclization under basic conditions, to afford the fused hydantoin. Mechanistic caveats, dependent on aldehydes of choice will be revealed and a facile oxidation of final products to imidazolidenetriones briefly discussed.
摘要
以下文章描述了一系列与乙内酰脲环稠合的4,5-二氢-1H-苯并[e][1,4]二氮杂卓的简洁合成方法。分子复杂度和生物学相关性较高，仅通过三步反应即可生成相应结构，利用乌吉反应来组装多种试剂。该方案代表了一种在乌吉-5-组分CO(2)介导的缩合反应中采用的新型UDC（乌吉-脱保护-环化）策略，随后在碱性条件下进一步环化，以得到稠合的乙内酰脲。取决于所选用的醛的机理注意事项将被揭示，并且还将简要讨论最终产物向咪唑啉三酮的简便氧化反应。
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