Improved Arndt-Eistert Synthesis of α-Diazoketones Requiring Minimal Diazomethane in the Presence of Calcium Oxide as Acid Scavenger
Vittorio Pace, Guido Verniest, Josep-Vicent Sinisterra, Andrés R. Alcántara* and Norbert De Kimpe
*Organic and Pharmaceutical Chemistry Department, Pharmacy
Faculty, Complutense University of Madrid, Pza. Ramón y Cajal s/n, 28040 Madrid,
Spain, Email: andresr
farm.ucm.es
V. Pace, G. Verniest, J.-V. Sinisterra, A. R. Alcántara, N. De Kimpe, J. Org. Chem., 2010, 75, 5760-5763.
DOI: 10.1021/jo101105g
Abstract
An improved Arndt-Eistert synthesis to obtain α-diazoketones allows the efficient transformation of acid halides using a stoichiometric amount of diazomethane in the presence of calcium oxide, without concomitant ketene or haloketone formation. The obtained α'-brominated-α-diazoketones were employed for the synthesis of interesting α-arylamino-α′-halomethylketones.
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Key Words
α-Diazoketones, Arndt-Eistert Synthesis
ID: J42-Y2010-2360
