摘要/Abstract
以炔烃-联烯酮为原料，水作为亲核试剂，通过N-氯代丁二酰亚胺（NCS）介导的[2+2]环加成和碳碳叁键断裂重组反应合成了18个2，4，4-三氯萘-1（4H）-酮衍生物，产率为55%~88%.所得产物的结构经NMR和IR以及HRMS等表征，其中目标产物2e的结构经X单晶分析确认.该反应条件温和、操作简单、无需金属催化剂且产率良好，为合成官能化的1-萘酮衍生物提供了一种新的高效的合成策略.
关键词: 炔烃-联烯酮, [2+2]环加成, 碳碳叁键断裂重组反应, 2,4,4-三氯萘-1(4H)-酮衍生物
N-Chlorosuccinimide (NCS)-mediated[2+2] cycloaddition and C-C triple bond cleavage/rearrangement reaction of yne-allenones and H2O as a nucleophilic reagent enabled the formation of 18 examples of 2,4,4-trichloronaphthalene-1(4H)-one derivatives with 55%~88% yields. The structures of these obtainable products were based on their NMR, IR and HRMS data, among which the structure of product 2e was confirmed by X-ray analysis. This metal-free transformation features mild conditions, simple operation and high reaction yields. It provides an effective and new protocol for the synthesis of trichloro-substituted naphthalene-1(4H)-ones.
Key words: yne-allenones, [2+2] cycloaddition, C-C triple bond cleavage/rearrangement, 2,4,4-trichloronaphthalene-1(4H)-ones
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