Pyrhi&e and@rtli&ne &liwtrv "esOf[bo]fuuerale havebeenOwinedbythermolysis of -~@-*ne *3wOle~fik PRSXUX OfC.SO. @ 1997ElsevierScienceLtd.
Cycloaddition reactiong speciallyDiels-Alderand 1,3-dipolar onex,havebeenthe methodof choicefor the preparationof a widerangeof neworganicderivativesof C~.' Manystudieswith C60involvingDiels-Alderreactionsuse o-quinodimethanes 1 as dienes.Thesehighly reactivespecies,whichcanbe generatedin situ ffoma largevarietyof precursors,vare efficiently trappedwith C60, whichbehavesas an electrondeficient dienophile.
In contrastto the frequentuse of o-quinodimethanes 1 for the derivatizationof ~their heterocyclic analogues2 havereceivedscantattention despitetheirversatilityforthe productionof heterocyclicderivatives of C60.To the best of our knowledge,the addition of thiophene,benzoh]thiophene,fhran and thiazole oquinodimethanederivativesto CiW are the onlyreportedexamplesin this area.4Now, we presentour results onthe additionof pyrimidine andpyrimidone o-quinodirnethanes (3 and4) to C60.
Recently,we have reportedthe synthesisof pyrimidine5 and pyrimidone6 fixed 3-sulfolenes. We found that these compounds,when refluxed in 1,2,4-trichlorob enzene, extrude SUMKdioxide generating the corresponding o-quinodimetbanes whichcan be trappedin Diels-Alderreactionswith variousdienophiles. We decidedto extendthat work to the synthesisof new Mlerene derivativeshavingpyrimidineand pyrimidone moieties.