Structural Studies on Febrifugine and Isofebrifugine. Alkaloids from Dichroa Febrifuga. Studies on 4-Quinazolones. Synthesis of Some 8-Aminoquinolines

Citation

Phillips, Robert Edward (1953) Structural Studies on Febrifugine and Isofebrifugine. Alkaloids from Dichroa Febrifuga. Studies on 4-Quinazolones. Synthesis of Some 8-Aminoquinolines. Dissertation (Ph.D.), California Institute of Technology. doi:10.7907/QQS1-H154. https://resolver.caltech.edu/CaltechETD:etd-05122003-110549

Abstract

NOTE: Text or symbols not renderable in plain ASCII are indicated by [...]. Abstract is included in .pdf document. Structural studies on two isomeric, antimalarial alkaloids, febrifugine and isofebrifugine, isolated from Dichroa febrifuga, have been continued. The basic structure of both alkaloids is proposed to be 3-[[Beta]-keto ?[gamma]-(3-hydroxy-2-piperidyl)propyl]-4-quinazalone, and the relationship of febrifugine and isofebrifugine to this structure is discussed. Febrifugine is shown to be polymorphic, and evidence is presented that the alkaloid [gamma]-dichroine, from Dichroa febrifuga, is not chemically distinct, but a mixture of two of the crystalline modifications of febrifugine. The synthesis of some 3-substituted-4-quinazolones is described. These are shown to be unreactive to benzenesulfonyl chloride, while the parent substance, 4-quinazolone, forms 3-benzenesulfonyl-4-quinazolone. The structure of a hydrolysis product of the letter compound is proposed to be N-(N?-formyl-[?]-aminobenzoyl) benzenesulfonamide, and the synthesis of this and of some related compounds is described. The synthesis of some 8-aminoquinolines related to isoplasmocid was carried out as part of a cooperative project to study to study their action on experimental poliomyelitis in monkeys. These compounds were tested elsewhere and found to be without specific activity.

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