Reactions of Strychnine and Its Derivatives

In his thorough study of the iV-methyl-pseudostrychnine derivates, Boit (318) investigated the reaction of lithium aluminum hydride on these compounds and showed that both iV-methyl-sec-pseudostrych-nine (CCIV, R=H) and iV -methyl-sec-pseudostrychnidine gave the same product (CCV, R=H), which showed no carbonyl absorption in the infrared but did show a band at 3.Op, due to the hydroxyl group, which could be made to react with phenyl isocyanate to form a crystalline urethan. The same results were produced in the brucine series 

Osmium tetroxide alone, or hydrogen peroxide with osmium tetroxide as catalyst, oxidizes strychnine to the expected glycol, CCVII, which 

Investigations have been made on the phenoxazine formation from this quinone (XCIII) with ammonia. The product, called Brucine Blue, is formulated as CCXI and is said to be identical with a product 

Analogous changes were observed in other neo-bases, in one of which the compound corresponding to CCXV was reduced back to the neo-series by zinc and hydrochloric acid. If this sequence should prove correct, it would provide an interesting addition to the known collection of acid-catalyzed rearrangements, but further experiment is clearly indicated before this scheme can be considered to be fully established. 

It aj)pears now that the formulation of the iV-methyl-sec-pseudo-strychnine metho-salts as -dimethyl derivatives (CCXXVI) was quite unjustified and that the postulation of the facile and unique migration of a methyl group from nitrogen to oxygen and back (cf. Vol. II, 525-527) that was to account for their behavior may now be dispensed with, leaving us with a less remarkable story perhaps but one which is more in harmony with contemporary theory. 

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