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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

Article DOI: 10.3791/60201-v • 07:30 min • January 21st, 2020
January 21st, 2020 •
1, 1, 1, 1, 2, 1
1Dipartimento di Scienza e Alta Tecnologia, Università degli Studi dell'Insubria, 2Department of Chemistry and Biochemistry, University of Oklahoma, Stephenson Life Sciences Research Center

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Summary
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.

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Direct Regioselective Atom-economical Synthesis 3-Aroyl-N-hydroxy-5-nitroindoles Cycloaddition 4-Nitronitrosobenzene Alkynones N-hydroxy 3-aroyl Indole Compounds Antibiotics Antinociceptics Antidiabetes Drugs Anticancer Drugs Stable Library N-hydroxyindole Derivatives Nitrosamines Alkynes Substituted Indole Products Synthetic Organic Chemistry 1-phenyl-2-propyne-1-one Synthesis Acetone 1-phenyl-2-propyne-1-ol Open Air Round Bottom Flask Magnetic Stirring Bar Jones Reagent 2-propanol Hexavalent Chromium Reactant Diatomaceous Earth
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