A new guanidinylation procedure for the preparation of functionalized guanidines and investigations towards the synthesis of cyclic guanidine compounds.

摘要

This thesis is a summary of research conducted since October 2000 at the University of Toronto in the laboratory of Dr. Robert A. Batey. This manuscript is divided into three chapters. Chapter one provides a brief introduction to the guanidine functional group and guanidine-containing compounds, both natural and synthetic.; Chapter two describes a new method for alkylation of guanidine-containing compounds using a convenient and mild biphasic protocol. This approach requires limited purification of the obtained products, yielding highly functionalized guanidines in good to excellent yields. This protocol has been used with a variety of alkyl halides and mesylates and provides an alternate approach to methods currently utilized in the literature.; Chapter three describes investigations towards the synthesis of cyclic guanidine compounds. Initially, iodocyclization reactions were attempted; however, limited success was encountered with this approach. Palladium-catalyzed π-allyl chemistry was then investigated to synthesize the cyclic guanidine compounds. Thus far, investigations with this approach have been successful and a general approach for the synthesis of cyclic guanidine compounds using palladium π-allyl chemistry is described for the first time within our labs.