4.7 Article

Multicomponent Cascade Reaction of 3-Cyanochromones: Highly Site-Selective Synthesis of 2-(1H-Imidazol-1-yl)-4H-chromen-4-one Derivatives

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 87, Issue 22, Pages 15187-15196

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.2c01719

Keywords

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Funding

  1. Major Science and Technology Projects in Yunnan Province [2019FY003003]
  2. National Natural Science Foundation of China [21662042]
  3. theScientific and Technological Innovation Team of Green Synthesis and Activity Research of Natural-like Heterocyclic Compound Libraries in Uni-versities of Yunnan Province [C17624011121]
  4. Postgraduate Scientific Research Innovation Project of Yunnan University [2021Y042]

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A method for the synthesis of 2-(1H-imidazol-1-yl)-4H-chromen-4-one derivatives (IMCMs) was developed through a one-pot cascade reaction, involving various reactions such as 1,2-addition, Michael reaction, ring-closing, tautomerization, ring-opening, and [3 + 2] cyclization. This strategy not only enabled the synthesis of functionalized imidazoles (IMCMs), but also the synthesis of useful enamine building blocks, making it suitable for combinatorial and parallel syntheses of IMCMs.
A method for the synthesis of 2-(1H-imidazol-1-yl)-4H-chromen-4-one derivatives (IMCMs) from 3cyanochromones and alpha-isocyanoacetates via a one-pot cascade reaction involving a 1,2-addition, Michael reaction, ring-closing, tautomerization, ring-opening, and [3 + 2] cyclization was enabled by refluxing a mixture of the starting materials in THF in the presence of Ag2CO3 as a catalyst. The cascade reaction resulted in the formation of five bonds and the cleavage of two bonds, including a triple bond, in one pot. This protocol enabled not only the synthesis of functionalized imidazoles (i.e., IMCMs) but also the synthesis of functionally useful enamine building blocks. This strategy is suitable for combinatorial and parallel syntheses of IMCMs.

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