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A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
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JoVE Journal Chemistry
A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

DOI:
10.3791/60201-v

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07:30 min

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January 21, 2020

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, , , , ,
1Dipartimento di Scienza e Alta Tecnologia,Università degli Studi dell’Insubria, 2Department of Chemistry and Biochemistry,University of Oklahoma, Stephenson Life Sciences Research Center

Chapters

  • 00:05Title
  • 01:021-Phenyl-2-Propyne-1-One Synthesis
  • 02:294-Nitronitrosobenzene Preparation
  • 03:373-Benzoyl-1-Hydroxy-5-Nitroindole Synthesis
  • 04:48Results: Representative 3-Aroyl-N-Hydroxy-5-Nitroindole Synthesis
  • 06:32Conclusion

Summary

Automatic Translation

Automatic Translation

3-Aroyl-N-hydroxy-5-nitroindoles were synthesized by cycloaddition of 4-nitronitrosobenzene with a conjugated terminal alkynone in a one-step thermal procedure. Preparation of the nitrosoarene and of the alkynones were adequately reported and respectively through oxidation procedures on the corresponding aniline and on the alkynol.

Tags

Keywords: 3-aroyl-N-hydroxy-5-nitroindolesCycloaddition4-nitronitrosobenzeneAlkynononesN-hydroxyindolesRegioselective SynthesisAtom-economicalAntibioticsAntinocicepticsAntidiabetesAnticancer DrugsNitrosaminesAlkynes1-phenyl-2-propyne-1-oneJones Reagent4-nitroanilinePotassium Peroxy Monosulfate

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