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Synthesis of 1-Iodo-substituted Codeine Derivatives

[ Vol. 15 , Issue. 12 ]

Author(s):

Sándor Hosztafi*, Márta Kraszni, GergÅ‘ Tóth and János Marton   Pages 1012 - 1020 ( 9 )

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.

Affiliation:

Department of Pharmaceutical Chemistry, Semmelweis University, Hogyes Endre utca 9, H-1092 Budapest, Department of Pharmaceutical Chemistry, Semmelweis University, Hogyes Endre utca 9, H-1092 Budapest, Department of Pharmaceutical Chemistry, Semmelweis University, Hogyes Endre utca 9, H-1092 Budapest, ABX Advanced Biochemical Compounds Biomedizinische Forschungsreagenzien GmbH, Heinrich-Glaeser-Strasse 10- 14, D-01454 Radeberg

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