Madelung synthesis

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The Madelung synthesis is a chemical reaction that produces (substituted or unsubstituted) indoles by the intramolecular cyclization of N-phenylamides using strong base at high temperature.

This method is essentially confined to the preparation of 2-alkinylindoles (not easily accessible through electrophile aromatic substitution) because of the vigorous reaction conditions.

References

  • Madelung, W.; Ber. 1912, 45, 1128.
  • Houlihan, W. J. et al.; J. Org. Chem. 1981, 46, 4511, 4515.

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