Methyl-substituted trans-1,2-cyclohexanediamines as new ligands for oxaliplatin-type complexes |
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Authors: | Ladislav Habala Alexey A Nazarov Christian G Hartinger Sergey A Abramkin Wolfgang Lindner Bernhard K Keppler |
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Institution: | a Institute of Inorganic Chemistry, University of Vienna, Waehringer Strasse 42, A-1090 Vienna, Austria b Institute of Analytical Chemistry, University of Vienna, Waehringer Strasse 38, A-1090 Vienna, Austria |
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Abstract: | Three different pathways for the synthesis of substituted trans-(±)-1,2-cyclohexanediamines as new ligands for oxaliplatin-type compounds are presented. The different synthetic routes lead (i) by the synthesis of the compound via ortho-bromination of a substituted cyclohexanone followed by reaction with hydroxylamine and reduction by hydrogen, (ii) by addition of azide to cyclohexene mediated by manganese(III) acetate and reduction by hydrogen, or (iii) by trans-dihydroxylation of cyclohexene, and subsequent conversion into the respective mesylate or tosylate, followed by substitution by azide, and reduction in the case of 4-methyl-trans-(±)-1,2-cyclohexanediamine to a preferentially equatorially, mainly axially, or exclusively equatorially or axially oriented 4-methyl group, respectively. |
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