Year
1968
Degree Name
Bachelor of Science (Hons.)
Recommended Citation
Summons, Roger Evertt, The synthesis of phenanthropiperidines, Bachelor of Science (Hons.) thesis, , University of Wollongong, 1968. https://ro.uow.edu.au/theses/908
Abstract
In order to develop a facile preparative method for the synthesis of the physiologically active alkaloid tylocrebrine and its analogues, and to further examine the relationships between chamical structure and physiological activity, a new approach to the preparation of phenanthropiperidines and phenanthroindolizidines was devised and investigatedo Michael reactions between methoxyl substituted ethyl cinnamates and phenylacetonitriles proceeded smoothly to yield four new ethyl- if -cyano- ^ , ^ - diphenylbutyrateso These compounds underwent- reductive cyclisation by catalytic high pressure hydrogénation to give the corresponding N-ethyl 3, 4-diphenylpiperidines in good yield. The mechanism of the reduction reaction was elucidated and found to proceed via an oC -piperidone, which is further reduced to a secondary amine, and then alkylated at the nitrogen by the alcohol present as solvent©
Unless otherwise indicated, the views expressed in this thesis are those of the author and do not necessarily represent the views of the University of Wollongong.