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A new synthetic route to the azocino[4,3‐ b ]indole core structure
Author(s) -
Patir Süleyman
Publication year - 1995
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.1995199508214
Subject(s) - chemistry , imine , strychnos , indole test , ketone , amine gas treating , derivative (finance) , aldol reaction , substructure , organic chemistry , stereochemistry , combinatorial chemistry , alkaloid , catalysis , financial economics , economics , structural engineering , engineering
The reaction of 2 with 2‐methoxyethylamine in the presence of ZnCl 2 afforded imine 3 , which was reduced with NaBH 4 to amine 4 without isolation. After deprotection of the carbonyl function by treatment with benzeneseleninic anhydride, ketone 5 was converted to compound 6 with 2‐oxobutyric acid and dicyclohexylcarbodiimide. The isodasycarpidone derivative 7 , formed by aldol reaction of 6 , represents a tetracyclic substructure of strychnos‐type alkaloids.