Synthesis of a Novel Class of β-Lactam Derivatives of 1-Aminophosphonates by Staudinger Ketene-Imine [2+2]-Cycloaddition Reaction

Abstract

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.

Ketenes and Other Cumulenes as Reactive Intermediates

“…94 Ketenes generated by acyl chloride dehydrochlorination give [2 + 2] cycloaddition with imines bearing a phosphonatesubstituted side chain forming the corresponding β-lactams (eq 95). 95 Generation of seleno-substituted ketenes using Vilsmeier dehydration of carboxylic acids and [2 + 2] cycloaddition with imines provides a route to selenium-substituted trans-β-lactams (eq 96). 96 Substituted proline derivatives with activation by Mukaiyama's reagent give ketenes that form a diastereomeric mixture of pyrrolidine-derived spiro-β-lactams (eq 97).…”

“…Ketenes generated by acyl chloride dehydrochlorination give [2 + 2] cycloaddition with imines bearing a phosphonate-substituted side chain forming the corresponding β-lactams (eq ) …”

Synthesis, characterization, and antifungal activity of novel inulin derivatives with chlorinated benzene

“…The crude products were purified by crystallization from ethanol. (Kaboudin, Afsharinezhad, & Mohammad, 2010).…”