Synthesis of 1-Iodo-substituted Codeine Derivatives

Title:Synthesis of 1-Iodo-substituted Codeine Derivatives

Volume: 15 Issue: 12

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

Affiliation:

• Department of Pharmaceutical Chemistry, Semmelweis University, Hogyes Endre utca 9, H-1092 Budapest,Hungary

Keywords: 1-iodocodeine analogues, 1-iodomorphine, 1-iododihydromorphine, 3, 6-di-O-acetyl-1-iodomorphine, 8- iodoapocodeine, aryl iodides.

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.

Cite this article as:

Hosztafi Sándor *, Kraszni Márta , Tóth Gergő and Marton János , Synthesis of 1-Iodo-substituted Codeine Derivatives, Letters in Organic Chemistry 2018; 15 (12) . https://dx.doi.org/10.2174/1570178615666171222163442