First SNAr reaction using TDAE-initiated carbanions in quinazoline series

✍ Scribed by Marc Since; Omar Khoumeri; Pierre Verhaeghe; Martine Maillard-Boyer; Thierry Terme; Patrice Vanelle

• Book ID: 104099300
• Publisher: Elsevier Science
• Year: 2011
• Tongue: French
• Weight: 407 KB
• Volume: 52
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/j.tetlet.2011.05.060

✦ Synopsis

We report herein the first example of a S N Ar reaction using TDAE-initiated carbanions in quinazoline series. The o-nitrobenzyl carbanion, formed by the action of TDAE on o-nitrobenzyl chloride, reacts with 4-chloro-2-trihalomethylquinazolines 4 and 5 via a S N Ar mechanism. This enabled a new series of 4benzyl-2-trihaloquinazoline derivatives to be synthesized in good yields under mild reaction conditions offering promising prospects for pharmacomodulation.