Grignard reagents benzamide

Hydroxyquinazolines react with primary amines or hydrazines to form 3-substituted 4(3//)quinazolinones (15). > The mechanism was shown to involve ring opening because with secondary amines (where ring closure is not possible) A-disubstituted benzamides are formed. Grignard reagents do not always react in the normal way with... 

Conjugate addition-elimination. The displacement of the o-(r-butylsulfonyl) group of benzamides with aryl Grignard reagents furnishes unsymmetrical biphenyls. ... 

Cook reported the iron/diphosphine-catalyzed alkylation of arene-, heteroarene-, and alkeneamides with primary alkyl halides (Eq. 19) [53] and, shortly after, the alkylation of aromatic amides with benzyl chlorides and secondary alkyl bromides (Eq. 20) [54]. The reaction with primary alkyl bromides proceeded well for aromatic, heteroaromatic, and alkenyl amides despite using phenylmagnesium bromide as a base, the reaction with benzyl chlorides proceeded well under air. As previously observed by Nakamura [28, 34], the slow addition of the Grignard reagent was crucial in order to achieve high yields, presumably because of the competing homocoupling [29]. Secondary alkyl bromides and iodides could be employed in the reaction with benzamides, but acyclic secondary alkyls underwent partial isomerization to the linear alkyl. 

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