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Metal Free Access to Polysubstituted Pyrimidines via Nitrile Activation and [2+2+2] Cycloaddition.

Jinkui ChaiYu NieZhao WangLi ChengYing-Guo LiuJunliang Wu
Published in: Chemistry (Weinheim an der Bergstrasse, Germany) (2021)
Tf2 O mediated intermolecular / intramolecular [2+2+2] cycloaddition between alkynes and nitriles has been developed for efficient construction of polysubstituted pyrimidines and bicyclopyrimidines. In presence of Tf2 O, aza-allene species were generated in situ through nitrile activation and subsequently participated in the [2+2+2] cycloaddition, which was fully supported by deuteration experiments. The reaction had good substrate extensibility with moderate to excellent yield including trimethylsilylalkynes. The method was utilized as a synthetic tool in the preparation of a luminescent metal complex.
Keyphrases
  • energy transfer
  • sensitive detection
  • molecularly imprinted
  • metal organic framework
  • mass spectrometry
  • genetic diversity
  • liquid chromatography