Hydrastine imide

Adlumidine, (-)>adlumilantine, (-)-adlumine, (+)-bicuculline, cryptopine, fumaramine, fumaridine (=hydrastine imide), 109, 111, 171,... 

Adlumiceine, adlumiceine enol lactone, adlumidiceine, adlumidiceine enol lactone, bicucullinidine, bicucullinine, fumaramidine, fumaramine, fumaridine (= hydrastine imide), fumschleicherine, A-methylhydrasteine, IV-methylhydrastine, narceine imide, narceine imine, narlumidine, A-methyloxohydrasteine... 

Fumaridine (= hydrastine imide) (349) Fumschleicherine (351) iV-Methylhydrasteine (339) N-Methylhydrastine (336) W-Methyloxohydrasteine (344)... 

Fumaridine and fumaramine have now been shown to be phthalideiso-quinolines as indicated above, rather than protopines, as previously believed thus fumaridine corresponds to the known compound hydrastine imide. ... 

A series of N-substituted narceine amides (Section III,D,1) was prepared from 101 under the action of primary amines (100). Acid-catalyzed dehydration transformed these amides to corresponding imides (ene lactams) of the ( )-narceine imide (117) type (100). Similar transformations were performed in the hydrastine series (101). JV-Methylhydrastine (98) when treated with dilute ammonium hydroxide gave hydroxy lactam 127, which was dehydrated to (Z)-fumaridine (113) (5). Sodium borohydride was able to reduce the stilbene double bond in 98 to produce saturated lactone 132 (5). 

Ene lactams can be obtained directly from quaternary phthalideisoquino-linium salts by treating them with concentrated ammonium hydroxide. In this way fumaramine (111) was synthesized from bicuculline (88) methiodide (121,124), fumaridine (113) from methiodides of both diastereomeric / - (91) and a-hydrastines (92) (5,124-126), and narceine imide (116) from narcotine (94) methiodide (122,127,128). In the case of the hydrastines (91 and 92) the Hofmann degradation of their methiodides in ammonia was not stereospecific but yielded the thermodynamically more stable Z isomer (113) (5). It seems, however, that from narcotine (94) a mixture of the Z and E forms was produced rather than a single isomer (123,127). 

A simple synthesis of racemic cordrastine and hydrastine can be accomplished by condensation of 3,4-dihydro-6,7-dimethoxy-2-methyl- or 3,4-dihydro-6,7-methylenedioxy-2-methylisoquinolinium salts with methyl-6-diazomethyl-2,3-dimethoxybenzoate, derived from 6,7-dimethoxyphthal-imide (697). 

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