Premium
Synthesis of 1‐Aminocodeine as a Synthon for Other Codeine Derivatives
Author(s) -
Cankař Petr,
Popa Igor,
Trávníček Zdeněk,
Stýskala Jakub,
Hradil Pavel,
Slouka Jan
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201300701
Subject(s) - chemistry , nitration , synthon , codeine , derivative (finance) , organic chemistry , combinatorial chemistry , stereochemistry , medicine , morphine , economics , pharmacology , financial economics
The first nitration of codeine by using bismuth nitrate pentahydrate under mild reaction conditions is described. The resulting 1‐nitrocodeine was reduced to 1‐aminocodeine, a key precursor for the synthesis of the azo derivative and several hydrazones. Structures of both 1‐nitrocodeine and 1‐aminocodeine were unequivocally determined by single‐crystal X‐ray analysis. The reported preliminary synthetic study lays the groundwork for the synthesis of modified codeine derivatives with potential biological activity.