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Base-Catalyzed Cascade Cyclization of 2-Nitrochalcones and Isocyanides to Access Pyrano[3,4- b ]indol-1(9 H )-one Frameworks.

Juan WanGuiyun ZengShuntao HuangYilong YuanZhuoting XuYuanmin WenChao Huang
Published in: The Journal of organic chemistry (2024)
An unexpected cascade reaction of 2-nitrochalcones with isocyanoacetates has been reported for the efficient synthesis of indole carboxylic esters and pyranoindoles. The conversion was achieved by KOH-catalyzed cyclization and elimination of the nitro group with final decarbonylation-aromatization. The method was used to synthesize a series of potentially biologically active indole derivatives (49 examples) in 67-85% yields under transition-metal-free catalytic conditions.
Keyphrases
  • room temperature
  • ionic liquid
  • crystal structure