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

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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

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

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There are several other

References

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  • 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.

Category:Indole forming reactions Category:Carbon-heteroatom bond forming reactions

Category:Name reactions