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The Nenitzescu indole synthesis is a chemical reaction that forms 5-hydroxyindole derivatives from benzoquinone and β-aminocrotonic esters.

The Nenitzescu indole synthesis
The Nenitzescu indole synthesis

Mechanism

The mechanism of a Nenitzescu reaction consists of a conjugate addition, followed by a nucleophilic attack by the C–N pi bond, and then an elimination.

Mechanism for the Nentizescu Indole Synthesis
Mechanism for the Nentizescu Indole Synthesis

The reaction was first published by Nenitzescu in 1929,[1] and since then...

There are several other

References

  • Nenitzescu, C. D. Bull. Soc. Chim. Romania 1929, 11, 37.
  • Allen, Jr., G. R. et al. J. Am. Chem. Soc. 1966, 88(11), 2536–2544. PMID 5941382
  • Allen, Jr., G. R. Org. React. 1973, 20, 337.
  • Pawlak, J. M. et al. J. Org. Chem. 1996, 61, 9055.
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Category:Indole forming reactions Category:Carbon-heteroatom bond forming reactions

Category:Name reactions

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