First SN Ar reaction using TDAE-initiated carbanions in quinazoline series

M Since, O Khoumeri, P Verhaeghe, M Maillard-Boyer…

Index: Since, Marc; Khoumeri, Omar; Verhaeghe, Pierre; Maillard-Boyer, Martine; Terme, Thierry; Vanelle, Patrice Tetrahedron Letters, 2011 , vol. 52, # 29 p. 3810 - 3813

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Citation Number: 10

Abstract

Abstract We report herein the first example of a SN 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 SN Ar mechanism. This enabled a new series of 4-benzyl-2-trihaloquinazoline derivatives to be synthesized in good yields under mild reaction conditions offering promising prospects for ...