Iodination of 1,3-dihydroxy-10-methyl-9-acridone (2c) and its ethers 2a and 2b gave the corresponding 2-iodo derivatives 3a -c. Bromination of 2a with NBS yielded 2-bromo-(lo), 4-bromo-( l l ) , as well as small amounts of 2,4-dibromo-l,3-dimethoxy-10-methyl-9-acridone (12). Under the same conditions from 2c 2-bromo-l,3-dihydroxy-1O-methyl-9-acridone (13) has been obtained. Chlorination of 2a with S02C12 in CHCI, gave-4-chloro-(14) and 2,4-dichloro-l-hydroxy-3-methoxy-10-methyl-9-acridone (15). The reaction of 3 b with copper(1) phenyl-and copper(1) isopropenylacetylide yielded the corresponding 2-substituted 4-methoxy-6-methylfuro[2,3-a]acridin-11(6ff)-ones 6a and 6b, respectively. From the condensation reaction of 3c with 3-chloro-3-methyl-1-butyne noracronycine (8) has been obtained.
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