By R.H.F Manske, H.L. Holmes
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Additional resources for Alkaloids: v. 3: Chemistry and Pharmacology
In connection with their work on the synthesis of quininic acid and of cinchoninic acid, Kaufmann and his collaborators (178-180, 184) had prepared hyanc&-methoxyquinoline and 4-cyanoquinoline, obtained earlier by dehydration of cinchoninamide with thionyl chloride or with phosphorus pentoxide (209). Both products reacted with methylmagn d u m iodide in anisole solution and furnished methy1-(6-methoxy-P quinoly1)-ketone and methyl-(4quinolyl)-ketone respectively (210, 211). Like Rabe (206), these investigators were cognizant of the synthetic 43 T E E CHEMISTRY OF T E E CINCHONA ALKALOIDS possibilities of such derivatives, and were further impressed by the preeence of the alkylaminoethanol function as a common structural feature in the cinchona bases and in other physiologically active compounds, for example, adrenalin.
The significance of the compounds in connection with the stereochemistry of the cinchona alkaloids is discussed in Section 111. d. 6'. Dihydroquinidine has been demethylated to dihydrocupreidine (XCIX). Conversion of the phenolic base to the corresponding amine (C) by the Bucherer reaction, followed XCIX C by diazotization and reduction by hypophoaphorous acid, led to dihydrocinchonine (138). In a similar may, cupreine was converted to cinchonidine. These transformations proved rigorously the long-assumed relationships, 6'-methoxycinchonine = quinidine, and 6'-methoxycinchonidine = quinine.
V. Minor Alkaloids Epiquinine, epiquinidine, heteroquinine and quinotoxine have been isolated from cinchona preparations in very small quantities (101, 234, 235), but it is not certain that these materials are not artifacts. The dihydrobases corresponding to the major alkaloids, on the other hand, always accompany the vinyl bases (29, 236, 237), from which they are best separated by treatment with mercuric acetate (90, 238, 239). The phenolic base cupreine (= demethylquinine) is also a natural product (240-242).
Alkaloids: v. 3: Chemistry and Pharmacology by R.H.F Manske, H.L. Holmes