Iodine/Water-Mediated Oxidation of<i>o</i>-Alkynylaroyl Compounds and Application of the Products of Oxidation in the Synthesis of Nitrogen Heterocycles
作者:Karuppusamy Sakthivel、Kannupal Srinivasan
DOI:10.1002/ejoc.201300046
日期:2013.6
facile iodine/water-mediated oxidation of the triple bond of o-alkynylaroyl compounds to furnish tricarbonyl compounds is reported. The reaction proceeds through the formation of isochromenol intermediates by the assistance of the neighbouring aroyl group. The product tricarbonyl compounds are versatile synthetic precursors that, upon treatment with mono- and diamines, hydrazines and amino alcohols, afford
报道了一种简单的碘/水介导的邻炔基芳酰基化合物三键氧化以提供三羰基化合物。该反应通过在相邻芳酰基的帮助下形成异色烯醇中间体而进行。产物三羰基化合物是通用的合成前体,在用单胺和二胺、肼和氨基醇处理后,可提供各种杂环支架,如异吲哚啉酮、酞嗪、苯并咪唑异喹啉酮、喹喔啉和苯并咪唑-喹喔啉杂化化合物。讨论了上述杂环形成的机理方面。最后,报告了异吲哚啉酮天然产物马兜铃内酰胺 BII 的短合成路线。