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Scapinello, L., Maspero, A., Tollari, S., Palmisano, G., Nicholas, K.M. and Penoni, A. (2020) A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones. Journal of Visualized Experiments, 155, e60201.
https://doi.org/10.3791/60201

has been cited by the following article:

• TITLE: Further Developments on the Regioselective Synthesis of 3-Aroylindole Derivatives from C-Nitrosoaromatics and Alkynones: A Novel Synthetic Approach to Pravadoline, JWH-073, Indothiazinone Analogues and Related Compounds

  AUTHORS: Luca Scapinello, Federico Vavassori, Gabriella Ieronimo, Keshav L. Ameta, Giancarlo Cravotto, Marco Simonetti, Stefano Tollari, Giovanni Palmisano, Kenneth M. Nicholas, Andrea Penoni, Angelo Maspero

  KEYWORDS: Nitrosoarenes, Alkynones, Indoles, Cycoaddition, Annulation

  JOURNAL NAME: International Journal of Organic Chemistry, Vol.12 No.3, September 23, 2022

  ABSTRACT: An uncatalyzed and easily accessible synthetic approach for the preparation of 3-aroylindoles was investigated using nitrosoarenes and aromatic terminal ethynyl ketones. Indole derivatives were produced in good yields and excellent regioselectivity. Functionalizations of the indole products were carried out affording highly valuable and versatile compounds. The indolization protocol was studied as a fundamental step for the preparation of pravadoline and 1-butyl-3-(1-naphthoyl)indole (JWH-073), bioactive molecules showing antinociceptic properties.