This thesis describes attempts to synthesise ellipticines for biological assessment in acceptable yields. It begins with a re-investigation of a procedure recommended for the preparation of 9-aminoellipticine and demonstrates that it is unacceptable when applied to large scale work. Alternative constructions have been sought principally directed towards the formation of pyridylethylindoles which may be ring closed to ellipticines by the application of techniques commonly used in this laboratory. This study has culminated in a novel synthesis of 3-(3'-pyridyl)butanal and its indolisation with various arylhydrazines under the conditions of the Fischer reaction and in this way 7-methyl-, 7-fluoro-, 7-chloro- and 9-methoxyellipticines were synthesised.
|Date of Award||1981|