Fekner Tomasz, Gallucci Judith, Chan Michael K
Department of Chemistry, The Ohio State University, 100 W 18th Avenue, Columbus, OH 43210, USA.
Org Lett. 2003 Dec 11;5(25):4795-8. doi: 10.1021/ol035761w.
A wide range of 2-(2-nitrophenyl)-1H-benzimidazoles undergo high-yielding intramolecular S(N)Ar of nitrite with N-pendant alkoxides under mild conditions (DMF, rt). When this operationally simple process is carried out at elevated temperatures in the presence of excess NaH, the initially formed S(N)Ar products are converted to the corresponding N-vinyl-substituted 2-(2-hydroxyphenyl)-1H-benzimidazoles via base-catalyzed isomerization. [reaction: see text]
多种2-(2-硝基苯基)-1H-苯并咪唑在温和条件下（N,N-二甲基甲酰胺，室温）与N-侧链醇盐发生高产率的分子内亚硝酸盐亲核芳香取代反应（S(N)Ar）。当在过量氢化钠存在下于高温进行这个操作简单的过程时，最初形成的S(N)Ar产物会通过碱催化异构化转化为相应的N-乙烯基取代的2-(2-羟基苯基)-1H-苯并咪唑。[反应：见正文]
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