Synthesis of 1-Iodo-substituted Codeine Derivatives

Author(s): Sándor Hosztafi*, Márta Kraszni, Gergő Tóth, János Marton.

Journal Name: Letters in Organic Chemistry

Volume 15 , Issue 12 , 2018

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Abstract:

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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Article Details

VOLUME: 15
ISSUE: 12
Year: 2018
Page: [1012 - 1020]
Pages: 9
DOI: 10.2174/1570178615666171222163442
Price: $65

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