Oxygen-Substituted Isocyanates: Blocked (Masked) Isocyanates Enable Controlled Reactivity,Advanced Synthesis & Catalysis

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Oxygen-Substituted Isocyanates: Blocked (Masked) Isocyanates Enable Controlled Reactivity
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2017-10-18 01:00:52 , DOI: 10.1002/adsc.201701046
Ryan A. Ivanovich ₁ , Dilan E. Polat ₁ , André M. Beauchemin ₁

Affiliation

Oxygen-substituted isocyanates (O-isocyanates) are rare isocyanates with a reported propensity to trimerize, a side-reaction that severely limited their use in synthesis. Herein, the development of blocked (masked) O-isocyanate precursors that form this reactive intermediate in situ provide controlled reactivity, allowing the first examples of cascade reactions involving O-isocyanates. Complex hydroxylamine-derived hydantoins and dihydrouracil compounds can be rapidly assembled from α- and β-amino esters, illustrating the convenience of masked O-isocyanates as hydroxylamine derived building blocks. Evidence for the intermediacy of an O-isocyanate intermediate is provided.

中文翻译：

氧取代的异氰酸酯：封闭的（掩盖的）异氰酸酯可实现受控的反应性

氧取代的异氰酸酯（O-异氰酸酯）是稀有的异氰酸酯，据报道具有三聚化的倾向，这种副反应严重限制了它们在合成中的用途。本文中，原位形成该反应性中间体的封闭的（掩蔽的）O-异氰酸酯前体的发展提供了可控制的反应性，从而允许涉及O-异氰酸酯的级联反应的第一个实例。复杂的羟胺衍生的乙内酰脲和二氢尿嘧啶化合物可从α-和β-氨基酯快速组装，这说明了被掩盖的O-异氰酸酯作为羟胺衍生的结构单元的便利性。提供了O-异氰酸酯中间体的中间体的证据。

更新日期：2017-10-18

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