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Synthesis of Novel 1-(1,5-Diaryl-1,10b-Dihydropyrrolo- [1,2-A][1,2,4]Triazolo[3,4-C]Pyrazin-3-Yl)Ethanones Via 1,3-Dipolar Cycloaddition of Nitrilimine

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The 1,3-dipolar cycloaddition of nitrilimine, generated in situ from (Z)-N-aryl-2-oxopropanehydrazonoyl bromide and Et3N, to 3-arylpyrrolo[ 1,2-a]pyrazine afforded novel 1-(1,5-diaryl-1,10b-dihydropyrrolo[1,2-a][1,2,4]triazolo[3,4-c]pyrazin-3-yl)ethanones in moderate yields. The structures of all the products were characterized thoroughly by NMR, IR, and HRMS.

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Scheme 1
Figure 1
Scheme 2

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We are grateful to the National Natural Science Foundation of China (No. 21671063), Natural Science Foundation of Hunan Province, China (2017JJ1026) and the Hunan Provincial Education Department Scientific Research Fund (No. 18A192).

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Correspondence to Xiaofang Li.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2020, 56(1), 84–87

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Huang, Y., Ren, D., Yu, X. et al. Synthesis of Novel 1-(1,5-Diaryl-1,10b-Dihydropyrrolo- [1,2-A][1,2,4]Triazolo[3,4-C]Pyrazin-3-Yl)Ethanones Via 1,3-Dipolar Cycloaddition of Nitrilimine. Chem Heterocycl Comp (2020). https://doi.org/10.1007/s10593-020-02626-3

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Keywords

  • nitrilimine
  • pyrrolo[1,2-a]pyrazine
  • [1,2,4]triazolo[3,4-c]pyrazine
  • 1,3-dipolar cycloaddition