NUCLEOPHILIC-ADDITION OF 2'-DEOXYNUCLEOSIDES TO THE ORTHO-QUINONE METHIDES 10-(ACETYLOXY) AND 10-METHOXY-3,4-DIHYDRO-9(2H)-ANTHRACENONE

In an effort to understand the chemistry of quinone methides, two simple, omicron-quinone methides 10-(acetyloxy)- and 10-methoxy-3,4-dihydro-9(2H)-anthracenone (3 and 4) have been constructed and their reactions with 2'-deoxyguanosine and 2'-deoxyadenosine investigated. The quinone methides were stirred with 1.2 equiv of nucleoside in H2O/CH3CN to afford products of N(6) alkylation with deoxyadenosine (3, 38%; 4, 16% yield) and N(2) alkylation with deoxyguanosine (3, 27%; 4, 5% yield).