Central nervous system active compounds. XIII. The use of aminomethylene phthalides in the synthesis of phthalideisoquinoline alkaloids

1983 ◽  
Vol 36 (12) ◽  
pp. 2493 ◽  
Author(s):  
SI Clarke ◽  
B Kasum ◽  
RH Prager ◽  
AD Ward
Keyword(s):  
Central Nervous System ◽  
Nervous System ◽  
Acidic Solution ◽  
Reaction Sequence ◽  
Active Compounds ◽  
Naturally Occurring ◽  
Aqueous Acidic Solution

Dimethylaminomethyleneisobenzofuranones react with alkoxyphenylethylamines in aqueous acidic solution to give phthalide isoquinolines (tetrahydroisoquinolinylisobenzofuranones) in moderate yields. N-Methylation gives the naturally occurring phthalideisoquinoline alkaloids. A number of examples of this reaction sequence are reported, including the synthesis of (�)-cordrastine, (�)-corlumine and (�)-adlumine.

Central nervous system active compounds. XII. The synthesis and properties of 3-dimethylaminomethylene phthalides

1983 ◽  
Vol 36 (12) ◽  
pp. 2483 ◽  
Author(s):  
SI Clarke ◽  
B Kasum ◽  
RH Prager ◽  
AD War
Keyword(s):  
Central Nervous System ◽  
Nervous System ◽  
Acidic Solution ◽  
Dimethyl Acetal ◽  
Active Compounds ◽  
Dimethylamino Group ◽  
Hydroxy Groups

Isobenzofuran-l(3H)-one (phthalide), and its derivatives react with dimethylformamide dimethyl acetal to form 3-dimethylaminomethyleneisobenzofuran-1-one and minor amounts of the corresponding internal betaine 2-(2-carboxylatophenyl) ethynyltrimethylammonium. The use of t-butoxy- is(dimethylamino)methane allows the isolation of the corresponding aminal, which readily loses dimethylamine on recrystallization. The dimethylamino group in the title compounds is replaceable by amino, hydrazino or hydroxy groups in mildly acidic solution. 3-Formylphthalide, the tautomer of the last-named product, could be isolated as the 2,4-dinitrophenylhydrazone.

Central nervous system active compounds. VI. Reissert compounds as precursors of 1-(3-phthalidy1)isoquinolines

1981 ◽  
Vol 34 (1) ◽  
pp. 151 ◽  
Author(s):  
TV Hung ◽  
BA Mooney ◽  
RH Prager ◽  
AD Ward
Keyword(s):  
Central Nervous System ◽  
Nervous System ◽  
Phase Transfer ◽  
Active Compounds ◽  
Central Nervous System Depressant ◽  
Reissert Compounds

The reactions of isoquinoline and phthalazine Reissert compounds with phthalaldehydic acids and their derivatives have been investigated as a means of synthesizing 1-(3-phthalidyl)isoquinolines. Of a variety of conditions tried those involving phase transfer were found, in general, to be the most suitable. The products, which are analogues of the convulsant alkaloid bicuculline, showed weak central nervous system depressant activity.

Central nervous system active compounds. X. Some aspects of the photochemical rearrangement of N-alkylsuccinimides to hexahydroazepinones

1981 ◽  
Vol 34 (12) ◽  
pp. 2695 ◽  
Author(s):  
BA Mooney ◽  
RH Prager ◽  
AD Ward
Keyword(s):  
Central Nervous System ◽  
Nervous System ◽  
Side Reactions ◽  
Active Compounds ◽  
Photochemical Rearrangement

The synthetic potential for the photolysis of alkylsuccinimides to give 6-substituted hexahydroazepine-2,5-diones is investigated. The reaction generally proceeds poorly, particularly when phenyl, cyano or ethoxycarbonyl groups are present. Fragmentation and intramolecular disproportionation reactions are identified as major side reactions.

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