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

Scapinello, Luca and Vavassori, Federico and Ieronimo, Gabriella and Ameta, Keshav L. and Cravotto, Giancarlo and Simonetti, Marco and Tollari, Stefano and Palmisano, Giovanni and Nicholas, Kenneth M. and Penoni, Andrea and Maspero, Angelo (2022) 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. International Journal of Organic Chemistry, 12 (03). pp. 127-142. ISSN 2161-4687

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Official URL: https://doi.org/10.4236/ijoc.2022.123011

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.

Item Type:	Article
Subjects:	Universal Eprints > Chemical Science
Depositing User:	Managing Editor
Date Deposited:	02 Jan 2023 10:53
Last Modified:	07 May 2024 04:11
URI:	http://journal.article2publish.com/id/eprint/631

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