SYNTHETIC ANALOGS OF Peganum ALKALOIDS. I. SYNTHESIS OF METHOXY- AND HYDROXY-SUBSTITUTED DEOXYVASICINONES AND DEOXYPEGANINES

Article abstract of DOI:10.1007/BF00579645

6-Methoxy-, 7-methoxy-, and 8-methoxydeoxyvasicinones have been synthesized by the reaction of substituted (3-methoxy-, 4-methoxy-, and 5-methoxy-) anthranilic acids with α-pyrrolidone.The demethylation of these compounds has given the corresponding hydroxy-substituted analogs of deoxyvasicinone, and the reduction of the products obtained with zinc in hydrochloric acid has given the hydroxy- and methoxy- analogs of deoxypeganine. 8-Hydrooxydeoxypeganine dimethyl-, ethyl-, and butylcarbamates have been obtained by the carbamoylation of 8-hydroxydeoxypeganine.