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.