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
Luca Scapinello, Federico Vavassori, Gabriella Ieronimo, K. L. Ameta, G. Cravotto, Marco Simonetti, S. Tollari, G. Palmisano, K. Nicholas, A. Penoni, A. Maspero
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引用次数: 1
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 excel-lent 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 an-tinociceptic properties. times were registered; c product precipitated; d reaction carried out in dioxane; e product recrystallised; f product isolated by chromatography.
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