Microwave-Enhanced Synthesis of Phosphonoacetamides
An efficient microwave protocol is described for the Michaelis–Arbuzov synthesis of secondary and tertiary N-aryl (and alkyl) (diethylphosphono)acetamides 1, by reaction of chloro- and bromoacetamides with triethyl phosphite in the presence of catalytic amounts of
sodium iodide. Remarkable acceleration of the reaction (minutes vs. several hours) over conventional heating was achieved, together with improved product yields and purity, when bromoacetamides were employed as the substrates. Chloroacetamides were comparatively less reactive, leading to satisfactory
yields only when a high excess of the reagent was employed.
Keywords: Michaelis–Arbuzov reaction; microwaves; phosphonoacetamides; phosphorus compounds; sodium iodide
Document Type: Research Article
Affiliations: Departamento de Química Orgánica, Facultad de Farmacia y Bioquímica,CONICET, Buenos Aires, Argentina
Publication date: 01 March 2012
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