SYNTHESIS OF VARIOUS BENZIMIDAZOLONE DERIVATIVES

Various heterocyclic systems containing benzimidazolone scaffold have been synthesized using as starting materials substituted benzimidazol-2-ones prepared by condensation of ophenyldiamine and its derivatives with ethyl chloroformate acting as carbonyl source. The alkylating agents such as 1-(2-chloroethoxy)-2-chloroethane, 1,2-di-(2-chloroethoxy)ethane and dichloroethylamine hydrochloride reacted with benzimidazolones under liquid-solid phase transfer catalysis conditions leading to 1,3-disubstituated benzimidazolic compounds containing crown ethers or oxazolidinone moieties. Furthermore 1,3- dipropargylbenzimidazol-2-one reacted with azides using a copper catalyzed alkyne azide cycloaddition to afford exclusively 1,3-(1,4-disubstituted-1,2,3-triazol-4yl) methyl benzimidazolone regioisomers