Journal of Organic Chemistry
Journal of Organic Chemistry
4 years ago

Access to 8-Azachromones via Activation of C–H in N-Oxides

Access to 8-Azachromones via Activation of C–H in N-Oxides
Zhongli Yan, Dong Wang, Hairong Feng, Peng Yu, Zhenlin Liu, Linna Li
A concise and practical synthetic method has been developed for 8-azachromones, including 8-azaflavones, which have emerged as a promising class of compounds. Using commercially available nicotinates as the starting material, 8-azachromones were obtained in only three steps. The key intramolecular O-arylation reaction was achieved by nucleophilic attack of enolates to C2 of N-oxides under PyBrop or Ac2O activation conditions. These studies provide the basis for the access to 8-azachromones, enabling future work including the discovery and development of novel chromonoid drugs or other functional materials.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b02063

DOI: 10.1021/acs.joc.7b02063

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