Vincent-Rocan Jean-François, Derasp Joshua S, Beauchemin André M
Centre for Catalysis Research and Innovation, Department of Chemistry and Biomolecular Sciences, University of Ottawa, 10 Marie-Curie, Ottawa, ON K1N 6N5, Canada.
Chem Commun (Camb). 2015 Nov 25;51(91):16405-8. doi: 10.1039/c5cc07212c.
Carbon-substituted isocyanates and isothiocyanates are common building blocks in organic synthesis. In contrast, synthetic uses of N-substituted isocyanates and isothiocyanates are severely underdeveloped: few have been reported and their reactivity had not been compared. Herein, we compare the reactivity of blocked (masked) N-isocyanate and N-isothiocyanate precursors in cascade reactions. Divergent reactivity is observed with secondary propargylic and allylic systems, leading to new syntheses of imidazolones, thiazolidines, and a tool to form complex azomethine imines.
碳取代的异氰酸酯和异硫氰酸酯是有机合成中常见的结构单元。相比之下，N-取代异氰酸酯和异硫氰酸酯的合成用途严重未得到充分开发：报道的很少，且它们的反应活性尚未进行比较。在此，我们比较了在串联反应中受阻（掩蔽）的N-异氰酸酯和N-异硫氰酸酯前体的反应活性。在仲炔丙基和烯丙基体系中观察到不同的反应活性，从而实现了咪唑酮、噻唑烷的新合成方法以及一种形成复杂甲亚胺亚胺的工具。
