Chemistry of Phosphorus Ylides: Part 41 Synthesis of Antimicrobial Agents from the Reaction of Aminoantipyrine, Coumarin- and Quinoline-carbaldehyde with Phosphacumulene and Phosphaallene Ylides

Pyrrolo-pyrazoles were obtained from the reaction between phosphacumulenes and aminoantipyrine, while the reaction with the phosphaallene (hexaphenylcarbodiphosphorane ylide) afforded the azaphosphole and pyrazolo-phosphanylidene. The aminocoumarin carbaldehyde gave the chromeno-phosphanylidene and the chromeno-pyridinone, when it was allowed to react with phosphacumulenes. The reaction of chloroquinoline carbaldehyde with the phosphacumulenes, gave chloroquinoline phosphanylidenecyclobutane, while the reaction with phosphaallene resulted in the formation of oxaphosphetane, phosphanylidene ethenyl- and oxaphosphetyl-quinoline. The structure of cyclobutanedione was confirmed by X-ray crystallography. The antimicrobial activity of the new compounds is also reported.