Improved Arndt-Eistert synthesis of alpha-diazoketones requiring minimal diazomethane in the presence of calcium oxide as acid scavenger.
A practical methodology to obtain alpha-diazoketones through an improved Arndt-Eistert synthesis is described. The method 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 alpha'-brominated-alpha-diazoketones were employed as suitable substrates for the synthesis of interesting alpha-arylamino-alpha'-halomethylketones.
Pace
Vittorio
V
Organic and Pharmaceutical Chemistry Department, Pharmacy Faculty, Complutense University of Madrid, Spain.
Verniest
Guido
G
Sinisterra
Josep-Vicent
JV
Alcántara
Andrés R
AR
De Kimpe
Norbert
N
D017610:Calcium Compounds / Q000737:chemistry*; D003978:Diazomethane / Q000737:chemistry*; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010087:Oxides / Q000737:chemistry*; D013237:Stereoisomerism
D017610:Calcium Compounds; D007659:Ketones; D010087:Oxides; D003978:Diazomethane; C016538:lime