A novel class of b-lactam derivatives of 1-aminophosphonates was synthesized by Staudinger [2+2] cycloaddition reaction of ketenes with imines derived from 1-aminophosphonates. Treatment of aromatic aldehydes with ammonia and diethyl phosphite followed by a reaction with ketenes, which are generated from the appropriate acid chloride and a tertiary amine, gave a novel class of b-lactam derivatives of 1-aminophosphonates. The major or, in some cases, sole product of the cycloaddition is the cis-b-lactam.

We report here a novel and convenient method for the synthesis of α-ureidophosphonates through a one-pot reaction of three component condensation of aldehyde with urea and diethylphosphite under catalyst-free conditions in toluene at reflux. Treatment of aldeyhde with a mixture of urea and diethylphosphite gives a α-ureidophosphonate in moderate yield. The α-ureidophosphonate product was easily separated and crystallized from the reaction mixture.

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