- α-Keto Amides and 1,2-Diketones from N,N'-Dimethoxy-N,N'-dimethylethanediamide. A Synthetic and Mechanistic Investigation
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N,N'-Dimethoxy-N,N'-dimethylethanediamide (1), a 1,2-dicarbonyl synthon prepared from oxalyl chloride, undergoes nucleophilic displacements with Grignard reagents to provide α-keto amides 2-12 in 28-90percent yields.The synthon also undergoes double nucleophilic displacements with organolithium reagents to furnish symmetrical 1,2-diketones 15-23 in 15-84percent yields.A mechanism accounting for all the products from the reaction of 1 with nucleophiles has been proposed.Several control experiments were carried out to support the proposed mechanism.
- Sibi, Mukund P.,Marvin, Mali,Sharma, Rajiv
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p. 5016 - 5023
(2007/10/03)
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