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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: andresrfarm.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 (free Supporting Information)


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