A New Approach to the Synthesis of Highly Substituted 3-Pyrrolin-2-ones

Abstract

The base-promoted cyclization of internal N-propargylmalonamides in the presence of carbonate bases at room temperature or at 80 °C affords highly substituted 3-pyrrolin-2-ones in good yields.

Key words

cyclizations - 3-pyrrolin-2-ones - lactams - propargyl­amines - palladium

References

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27

For example, when the amide 3a obtained from the reaction of 1a with ethyl malonyl chloride was reacted with 3-iodo-benzotrifluoride in Et₃N-DMF at 50 °C for 5 h, in the presence of PdCl₂(PPh₃)₂, 4aa was obtained in 42% yield.

30

PdCl₂ (PPh₃)₂ can be used as catalyst with similar results.

31

Carried out using piperidine in place of Et₃N, with 0.04 equiv of Cul.