We have synthesized new N-demethyl-N-substituted derivatives (n-propyl, allyl) of 1-
iodocodeine and their 7,8-dihydro analogues starting from codeine. Key intermediates, 1-iodonorcodeine
and 1-iododihydronorcodeine were prepared from the corresponding 6-O-acetylated compounds using alpha-
chloroethyl chloroformate. 3-O-Demethylation of 1-iodocodeine and 1-iododihydrocodeine with
boron tribromide resulted in 1-iodomorphine and 1-iododihydromorphine, respectively. The latter
compounds were transformed to their 3,6-di-O-acetyl derivatives. 8-Iodoapocodeine was prepared
from 1-iodocodeine by acid-catalyzed rearrangement.
Keywords: 1-iodocodeine analogues, 1-iodomorphine, 1-iododihydromorphine, 3, 6-di-O-acetyl-1-iodomorphine, 8-
iodoapocodeine, aryl iodides.
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