A series of new quinazoline derivatives bearing a vinylic chloride group on the 2-position was prepared by using a consecutive SRN1 / ERC1 radical strategy.
First S N Ar Reaction Using TDAE-Initiated Carbanions in Quinazoline Series. -Treatment of o-nitrobenzyl chlorides with TDAE results in formation of carbanions which undergo SNAr reaction with 4-chloroquinazolines bearing trihalomethyl substituents to give the substituted derivatives (III). Under similar conditions, the -CCl3 group in substrates (IV) reacts with aldehyde (V) to produce α-chloroketones (VI). -(SINCE, M.; KHOUMERI, O.; VERHAEGHE, P.; MAILLARD-BOYER, M.; TERME, T.; VANELLE*, P.; Tetrahedron Lett. 52 (2011) 29, 3810-3813, http://dx.doi.org/10.1016/j.tetlet.2011.05.060 ; Lab. Pharmaco-Chim. Radicalaire, Fac. Pharm., Univ. Aix-Marseille, F-13385 Marseille, Fr.; Eng.) -Mais 44-161
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