利用碳碳叁键断裂重组反应合成2,4,4-三氯萘-1(4H)-酮衍生物

C—C Triple Bond Cleavage/Rearrangement Reaction for Accessing 2,4,4-Trichloronaphthalen-1(4H)-ones

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.

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.