Allylation of Azoles with Allyltributyltin via Unstable N-(Alkoxycarbonyl)azolium Salts

Article abstract of DOI:10.1021/jo00085a020

The one-pot reactions of imidazoles with allyltributyltin in the presence of alkyl chloroformates gave 2-allyl-1,3-bis(alkoxycarbonyl)-4-imidazolines in good yields.The reactions of thiazoles and oxazoles also proceeded in a similar manner.The instability of the intermediary quaternary salts required the nucleophiles to be added simultaneously with the chloroformate.Therefore, the reaction was specific for allyltributyltin, since it doesn't react with the carbonyl group of chloroformates.The dihydro allyl adducts thus obtained were aromatized with potassium ferricyanide under basic conditions to afford the corresponding 2-allylazoles.