4.5 Article

Diversely Substituted Imidazo[1,2-a]pyrazine-8-oxo-3-carbaldehydes: An Iodine-Mediated Cyclization/Oxidation Approach

期刊

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2013, 期 4, 页码 693-700

出版社

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201201150

关键词

Synthetic methods; Nitrogen heterocycles; Iodine; Oxidation; Cyclization; Cross-coupling; Alkynes

资金

  1. Fund for Scientific Research, Flanders, Belgium (FWO)
  2. Research Fund of the University of Leuven (KU Leuven)
  3. Erasmus Mundus External Cooperation Window (EMECW)

向作者/读者索取更多资源

A mild and efficient iodine-mediated intramolecular heteroannulation approach for the construction of the imidazo[1,2-a]pyrazinone core has been developed. Under ambient conditions, this metal-free protocol allows easy access to densely functionalized imidazo[1,2-a]pyrazinone-3-carbaldehydes or (aminomethyl)imidazo[1,2-a]pyrazinones from substrates containing terminal alkynes by cyclization and subsequent oxidation or amination. Further diversification may be introduced by using substrates containing an internal alkyne and/or Suzuki coupling after cyclization to generate polysubstituted (dihydro)imidazo[1,2-a]pyrazinones.

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