| Part I. Unsaturated five-membered ring lactones constitute a key structural element in certain natural products which display an unusual range of biological activity. One such member of this lactone group is 2,4(3H,5H)-furandione ((beta)-tetronic acid). The examination of the chemical versatility of this small molecule and its synthetic applicability constitute the basis of this investigation.; For this study, a reliable preparative method for 2,4(3H,5H)-furandione was needed. Such a method has been developed and is reported. A variety of 3-(arylmethylene)-2,4(3H,5H)-furandiones are prepared by the 1:1 condensation of (beta)-tetronic acid with substituted benzaldehydes. This reaction has been extended to heteroaromatic aldehydes as well. A study of the NMR of spectra of these products and (beta)-tetronic acid itself is included. The 3-(arylmethylene)-2,4(3H,5H)-furandione system is utilized to synthesize the novel condensed (10-(aryl)-4,10-dihydro-1H,3H-furo{lcub}3,4-c{rcub}-{lcub}1,5{rcub}benzothiazepin-1-one system. Further, the ring transformation of 3-(arylmethylene)-2,4(3H,5H)-furandiones to the substituted pyrazol-3-one system by reaction with hydrazines is demonstrated.; Some heteroannelation reactions of (beta)-tetronic acid with a variety of substituted 2-aminobenzophenones, 2-aminobenzaldehydes, and o-amino heteroaromatic aldehydes have been accomplished. The first 1:1 aldol condensation adduct of a ketone with (beta)-tetronic acid has been achieved using the vic-polyketones ninhydrin and alloxan.; Finally, progress towards the synthesis of the (alpha),(beta)-bisbenzylbutyrolactone lignan carbon skeleton from 2,4(3H,5H)-furandione has been accomplished.; Part II. The synthesis of 3-(3-carboxy-10,11-dihydro-5H-dibenzo-{lcub}a,d{rcub}cyclohepten-5-ylidene)-N,N-dimethyl-1-propamine as a hapten for the widely prescribed antidepressant Amitriptyline is described. This hapten was prepared for use in the development of a radioimmunoassay for Amitriptyline. It can be successfully coupled to human serum albumin and illicits a satisfactory antibody response when injected into laboratory animals. |
