Regioselective synthesis of new EWG-Bearing 3-benzoyl-2-phenylbenzofurans by one-pot intramolecular acylation/thermal cyclization of phosphoranes and their CB1 antagonist activity
Michela Begala
Supervision
;Rafaela MostallinoFormal Analysis
;Maria Paola CastelliPenultimate
Formal Analysis
;Giovanna Lucia DeloguLast
Formal Analysis
2024-01-01
Abstract
(Benzoylmethylene)triphenylphosphoranes are useful intermediates in the synthesis of 3-benzoyl-2-phenylbenzofurans. Under Wittig conditions, they allow the simultaneous preparation of two 3-acyl regioisomers. Starting from the o-[(benzoyloxy)benzylidene]triphenylphosphonium salt bearing electron withdrawing groups (EWGs) on the ortho-benzoyloxy ring (nitro, cyano and trifluoromethyl groups), we developed an improved regioselective synthetic strategy, via tandem ylide acylation and thermal cyclization of the acyl ylide intermediate. Using our optimized method, only one 3-acyl regioisomer was obtained and the yields were highly improved (up to 92 %) comparing to the previously reported method, expanding the scope of synthesis to a wide variety of new EWG-containing 3-benzoyl-2-phenylbenzofurans. The synthesized compounds were evaluated for their activity on CB1 receptors. In particular, some of these compounds displayed activity as CB1 antagonists.File | Size | Format | |
---|---|---|---|
Tetrahedron 154 (2024) 133880.pdf Solo gestori archivio
Type: versione editoriale
Size 853.91 kB
Format Adobe PDF
|
853.91 kB | Adobe PDF | & nbsp; View / Open Request a copy |
Proof 2024 of Regioselective synthesis of new EWG†-Bearing 3-benzoyl-2-phenylbenzofurans by one-pot intramolecular acylation_thermal cyclization of phosphoranes and their CB1 antagonist activity - Proof Central.pdf embargo until 05/02/2026
Type: versione post-print
Size 893.8 kB
Format Adobe PDF
|
893.8 kB | Adobe PDF | & nbsp; View / Open Request a copy |
Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.