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Studies on the syntheses of heteroeyelie compounds. Part DVI . Synthesis of oxynilidine and nitidine
Author(s) -
Kametani Tetsuji,
Kigasawa Kazuo,
Hiiragi Mineharu,
Kusama Osamu
Publication year - 1973
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570100107
Subject(s) - chemistry , aryne , oxime , mannich reaction , derivative (finance) , methylenedioxy , amine gas treating , organic chemistry , stereochemistry , medicinal chemistry , catalysis , alkyl , halogen , financial economics , economics
A benzyne type reaction of 1‐bromo‐3,4‐dimethoxybenzene (V) with 3,4‐dihydro‐6,7‐methylenedioxy‐I(2 H )naphthalenone (VI) gave the tetralone derivative VII, which was converted into the amine IX via the oxime VIII. A Mannich reaction of IX afforded the benzo[c]phen‐anthridine II which was then transformed into oxynitidine (I) and nitidine (IV).